NPASS Compound

Structure

CID307754 OpenBabel06191716112D 76 85 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 -9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -7.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9904 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.5885 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 30 1 0 0 0 0 10 37 2 0 0 0 0 11 13 1 0 0 0 0 11 31 1 0 0 0 0 12 14 1 0 0 0 0 12 36 1 0 0 0 0 13 40 1 0 0 0 0 14 41 1 0 0 0 0 15 22 2 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 32 2 0 0 0 0 17 29 1 0 0 0 0 17 33 1 0 0 0 0 18 34 1 0 0 0 0 18 42 1 0 0 0 0 19 35 1 0 0 0 0 19 43 1 0 0 0 0 20 38 1 0 0 0 0 20 44 1 0 0 0 0 21 39 1 0 0 0 0 21 45 1 0 0 0 0 23 2 1 1 0 0 0 23 31 1 0 0 0 0 23 65 1 0 0 0 0 24 3 1 1 0 0 0 24 36 1 0 0 0 0 24 66 1 0 0 0 0 25 4 1 1 0 0 0 25 50 1 0 0 0 0 25 67 1 0 0 0 0 26 5 1 1 0 0 0 26 51 1 0 0 0 0 26 68 1 0 0 0 0 27 6 1 1 0 0 0 27 54 1 0 0 0 0 27 69 1 0 0 0 0 28 7 1 1 0 0 0 28 55 1 0 0 0 0 28 70 1 0 0 0 0 29 46 2 0 0 0 0 30 47 2 0 0 0 0 30 52 1 0 0 0 0 31 56 1 1 0 0 0 32 46 1 0 0 0 0 32 57 1 0 0 0 0 33 48 1 0 0 0 0 33 58 1 6 0 0 0 34 54 1 0 0 0 0 34 59 1 1 0 0 0 35 55 1 0 0 0 0 35 60 1 1 0 0 0 36 71 1 1 0 0 0 37 47 1 0 0 0 0 37 72 1 0 0 0 0 38 50 1 0 0 0 0 38 73 1 1 0 0 0 39 51 1 0 0 0 0 39 74 1 1 0 0 0 40 65 1 0 0 0 0 40 73 1 6 0 0 0 41 66 1 0 0 0 0 41 74 1 6 0 0 0 42 69 1 0 0 0 0 42 71 1 1 0 0 0 43 70 1 0 0 0 0 43 72 1 1 0 0 0 44 67 1 0 0 0 0 44 75 1 1 0 0 0 45 68 1 0 0 0 0 45 76 1 1 0 0 0 46 49 1 0 0 0 0 47 53 1 0 0 0 0 48 49 2 0 0 0 0 48 53 1 0 0 0 0 49 52 1 0 0 0 0 50 61 1 6 0 0 0 51 62 1 6 0 0 0 52 63 2 0 0 0 0 53 64 2 0 0 0 0 54 75 1 6 0 0 0 55 76 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1070.47
Volume:	1035.138
LogP:	6.264
LogD:	3.171
LogS:	-5.719
# Rotatable Bonds:	12
TPSA:	292.83
# H-Bond Aceptor:	21
# H-Bond Donor:	9
# Rings:	10
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.051
Synthetic Accessibility Score:	6.784
Fsp3:	0.673
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097
MDCK Permeability:	0.0002147673803847283
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	93.4507064819336%
Volume Distribution (VD):	-0.363
Pgp-substrate:	10.418651580810547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.892

ADMET: Excretion

Clearance (CL):	1.248
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.379
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.614
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.964
Carcinogencity:	0.811
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.815

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC307754

Natural Product ID:	NPC307754
*Common Name:**	Landomycin S
IUPAC Name:	(6R)-1,6-dihydroxy-8-[(2S,4R,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3-methyl-5,6-dihydrobenzo[a]anthracene-7,12-dione
Synonyms:	Landomycin S
Standard InCHIKey:	WFCJJMKSDMLZFM-BCQNVFRGSA-N
Standard InCHI:	InChI=1S/C55H74O21/c1-22-15-29-17-33(58)48-49(46(29)32(57)16-22)52(63)30-9-8-10-37(47(30)53(48)64)72-43-19-35(60)55(28(7)70-43)76-45-21-39(51(62)26(5)68-45)74-41-14-12-36(24(3)66-41)71-42-18-34(59)54(27(6)69-42)75-44-20-38(50(61)25(4)67-44)73-40-13-11-31(56)23(2)65-40/h8-10,15-16,23-28,31,33-36,38-45,50-51,54-62H,11-14,17-21H2,1-7H3/t23-,24-,25+,26+,27+,28+,31-,33+,34+,35+,36-,38+,39+,40-,41-,42-,43-,44-,45-,50+,51+,54+,55+/m0/s1
SMILES:	Cc1cc(O)c2c(c1)C[C@H](C1=C2C(=O)c2c(C1=O)c(ccc2)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@@H](O[C@H]2CC[C@@H]([C@@H](O2)C)O[C@H]2C[C@@H](O)[C@@H]([C@H](O2)C)O[C@@H]2O[C@H](C)[C@H]([C@@H](C2)O[C@H]2CC[C@@H]([C@@H](O2)C)O)O)[C@@H]([C@H](O1)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668771
PubChem CID:	50993821
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21188999]
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6700.0	nM	PMID[462890]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1500.0	nM	PMID[462890]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC307754 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	1599
0.2-0.3	3398
0.3-0.4	8007
0.4-0.5	9249
0.5-0.6	6678
0.6-0.7	7871
0.7-0.8	5035
0.8-0.85	304
0.85-0.9	80
0.9-0.95	24
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC223735
0.9817	High Similarity	NPC198893
0.9817	High Similarity	NPC232818
0.9817	High Similarity	NPC314489
0.9691	High Similarity	NPC63470
0.9634	High Similarity	NPC315619
0.9524	High Similarity	NPC85316
0.9524	High Similarity	NPC197357
0.9512	High Similarity	NPC246274
0.9412	High Similarity	NPC292706
0.9412	High Similarity	NPC224557
0.9345	High Similarity	NPC289876
0.9325	High Similarity	NPC146837
0.9325	High Similarity	NPC278329
0.9235	High Similarity	NPC58538
0.9226	High Similarity	NPC203751
0.9212	High Similarity	NPC178281
0.9207	High Similarity	NPC101116
0.9207	High Similarity	NPC212099
0.9118	High Similarity	NPC66820
0.9118	High Similarity	NPC92403
0.9118	High Similarity	NPC102053
0.9118	High Similarity	NPC76112
0.9118	High Similarity	NPC170018
0.9023	High Similarity	NPC87583
0.9006	High Similarity	NPC475246
0.9006	High Similarity	NPC46958
0.9	High Similarity	NPC85368
0.896	High Similarity	NPC477860
0.896	High Similarity	NPC475161
0.8947	High Similarity	NPC3718
0.8944	High Similarity	NPC131405
0.8927	High Similarity	NPC48474
0.8902	High Similarity	NPC187441
0.8902	High Similarity	NPC283980
0.8895	High Similarity	NPC176246
0.8889	High Similarity	NPC199357
0.8862	High Similarity	NPC216752
0.883	High Similarity	NPC76128
0.883	High Similarity	NPC271385
0.883	High Similarity	NPC111536
0.883	High Similarity	NPC30432
0.883	High Similarity	NPC5029
0.881	High Similarity	NPC17432
0.8807	High Similarity	NPC241847
0.8795	High Similarity	NPC53139
0.8793	High Similarity	NPC114257
0.8793	High Similarity	NPC299149
0.8793	High Similarity	NPC277710
0.8793	High Similarity	NPC153578
0.8793	High Similarity	NPC72783
0.8779	High Similarity	NPC65118
0.8779	High Similarity	NPC213052
0.8771	High Similarity	NPC470199
0.8771	High Similarity	NPC314459
0.8757	High Similarity	NPC99216
0.8736	High Similarity	NPC115447
0.8736	High Similarity	NPC83331
0.8736	High Similarity	NPC470582
0.8736	High Similarity	NPC470581
0.8735	High Similarity	NPC177742
0.8728	High Similarity	NPC68381
0.8728	High Similarity	NPC186800
0.8728	High Similarity	NPC470667
0.8721	High Similarity	NPC183441
0.8713	High Similarity	NPC222455
0.8706	High Similarity	NPC178173
0.8693	High Similarity	NPC476203
0.8678	High Similarity	NPC475233
0.8674	High Similarity	NPC282474
0.8674	High Similarity	NPC470198
0.8674	High Similarity	NPC470193
0.8674	High Similarity	NPC470196
0.8674	High Similarity	NPC470200
0.8674	High Similarity	NPC470194
0.8674	High Similarity	NPC470197
0.8674	High Similarity	NPC316274
0.8674	High Similarity	NPC470195
0.8671	High Similarity	NPC154986
0.8659	High Similarity	NPC314672
0.8647	High Similarity	NPC478026
0.8647	High Similarity	NPC478020
0.8647	High Similarity	NPC478022
0.8636	High Similarity	NPC164047
0.8636	High Similarity	NPC470448
0.8636	High Similarity	NPC470453
0.8636	High Similarity	NPC470452
0.8629	High Similarity	NPC266513
0.8621	High Similarity	NPC63105
0.8621	High Similarity	NPC470583
0.8621	High Similarity	NPC19056
0.8613	High Similarity	NPC270027
0.8605	High Similarity	NPC259905
0.8596	High Similarity	NPC229817
0.8596	High Similarity	NPC475352
0.8596	High Similarity	NPC475220
0.8596	High Similarity	NPC178851
0.8596	High Similarity	NPC473686
0.8596	High Similarity	NPC221140
0.858	High Similarity	NPC212290
0.858	High Similarity	NPC245059
0.858	High Similarity	NPC84494
0.8563	High Similarity	NPC98776
0.8555	High Similarity	NPC472129
0.8555	High Similarity	NPC43434
0.8555	High Similarity	NPC298778
0.8547	High Similarity	NPC105591
0.8529	High Similarity	NPC187934
0.8529	High Similarity	NPC56735
0.8529	High Similarity	NPC97637
0.8529	High Similarity	NPC61594
0.8529	High Similarity	NPC190450
0.8523	High Similarity	NPC477682
0.8523	High Similarity	NPC477683
0.8521	High Similarity	NPC328093
0.8514	High Similarity	NPC146803
0.8514	High Similarity	NPC70862
0.8512	High Similarity	NPC208651
0.8512	High Similarity	NPC206641
0.8508	High Similarity	NPC264302
0.8508	High Similarity	NPC321046
0.8506	High Similarity	NPC257011
0.8506	High Similarity	NPC137871
0.8506	High Similarity	NPC9002
0.8506	High Similarity	NPC288152
0.8506	High Similarity	NPC13989
0.85	High Similarity	NPC205721
0.8497	Intermediate Similarity	NPC472133
0.8488	Intermediate Similarity	NPC70441
0.8485	Intermediate Similarity	NPC473966
0.8483	Intermediate Similarity	NPC293227
0.8483	Intermediate Similarity	NPC313452
0.8483	Intermediate Similarity	NPC473717
0.8483	Intermediate Similarity	NPC475662
0.8483	Intermediate Similarity	NPC473631
0.8483	Intermediate Similarity	NPC478001
0.848	Intermediate Similarity	NPC311850
0.848	Intermediate Similarity	NPC124155
0.848	Intermediate Similarity	NPC147596
0.848	Intermediate Similarity	NPC257566
0.8475	Intermediate Similarity	NPC473895
0.8471	Intermediate Similarity	NPC132737
0.847	Intermediate Similarity	NPC314687
0.8466	Intermediate Similarity	NPC255799
0.8457	Intermediate Similarity	NPC25724
0.8457	Intermediate Similarity	NPC168789
0.8457	Intermediate Similarity	NPC472054
0.8452	Intermediate Similarity	NPC148323
0.8452	Intermediate Similarity	NPC283480
0.8448	Intermediate Similarity	NPC241387
0.8448	Intermediate Similarity	NPC241874
0.8448	Intermediate Similarity	NPC478021
0.8448	Intermediate Similarity	NPC199079
0.8448	Intermediate Similarity	NPC210808
0.8448	Intermediate Similarity	NPC251144
0.8448	Intermediate Similarity	NPC470580
0.8443	Intermediate Similarity	NPC470331
0.8443	Intermediate Similarity	NPC185103
0.8439	Intermediate Similarity	NPC249977
0.8436	Intermediate Similarity	NPC318119
0.843	Intermediate Similarity	NPC470735
0.843	Intermediate Similarity	NPC329647
0.843	Intermediate Similarity	NPC280923
0.8427	Intermediate Similarity	NPC315221
0.8421	Intermediate Similarity	NPC475382
0.8421	Intermediate Similarity	NPC44947
0.8418	Intermediate Similarity	NPC475261
0.8418	Intermediate Similarity	NPC47191
0.8412	Intermediate Similarity	NPC246469
0.8412	Intermediate Similarity	NPC142860
0.8412	Intermediate Similarity	NPC97285
0.8412	Intermediate Similarity	NPC472320
0.8412	Intermediate Similarity	NPC271270
0.8409	Intermediate Similarity	NPC470454
0.8409	Intermediate Similarity	NPC198199
0.8409	Intermediate Similarity	NPC199533
0.8409	Intermediate Similarity	NPC102028
0.8409	Intermediate Similarity	NPC474345
0.84	Intermediate Similarity	NPC294501
0.84	Intermediate Similarity	NPC478002
0.8393	Intermediate Similarity	NPC82190
0.8393	Intermediate Similarity	NPC3449
0.8393	Intermediate Similarity	NPC192219
0.8393	Intermediate Similarity	NPC174599
0.8391	Intermediate Similarity	NPC61791
0.8391	Intermediate Similarity	NPC473202
0.8391	Intermediate Similarity	NPC175477
0.8391	Intermediate Similarity	NPC297195
0.8391	Intermediate Similarity	NPC191653
0.8391	Intermediate Similarity	NPC5319
0.8391	Intermediate Similarity	NPC105283
0.8391	Intermediate Similarity	NPC293629
0.8391	Intermediate Similarity	NPC43587
0.8391	Intermediate Similarity	NPC291795
0.8391	Intermediate Similarity	NPC207574
0.8382	Intermediate Similarity	NPC68592
0.8382	Intermediate Similarity	NPC298666
0.8382	Intermediate Similarity	NPC262222
0.8382	Intermediate Similarity	NPC475174
0.838	Intermediate Similarity	NPC321916

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC307754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	933
0.2-0.3	1760
0.3-0.4	2748
0.4-0.5	1988
0.5-0.6	932
0.6-0.7	309
0.7-0.8	88
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD8313	Approved
0.9118	High Similarity	NPD8312	Approved
0.8547	High Similarity	NPD7879	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7074	Phase 3
0.8249	Intermediate Similarity	NPD6559	Discontinued
0.8239	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD7808	Phase 3
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7054	Approved
0.8146	Intermediate Similarity	NPD7251	Discontinued
0.8095	Intermediate Similarity	NPD7696	Phase 3
0.8095	Intermediate Similarity	NPD7697	Approved
0.8095	Intermediate Similarity	NPD7698	Approved
0.809	Intermediate Similarity	NPD6797	Phase 2
0.8032	Intermediate Similarity	NPD6776	Approved
0.8032	Intermediate Similarity	NPD6777	Approved
0.8032	Intermediate Similarity	NPD6781	Approved
0.8032	Intermediate Similarity	NPD6778	Approved
0.8032	Intermediate Similarity	NPD6782	Approved
0.8032	Intermediate Similarity	NPD6780	Approved
0.8032	Intermediate Similarity	NPD6779	Approved
0.8021	Intermediate Similarity	NPD7701	Phase 2
0.8012	Intermediate Similarity	NPD8455	Phase 2
0.8	Intermediate Similarity	NPD7435	Discontinued
0.799	Intermediate Similarity	NPD7783	Phase 2
0.799	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3226	Approved
0.7979	Intermediate Similarity	NPD8151	Discontinued
0.7958	Intermediate Similarity	NPD7870	Phase 2
0.7958	Intermediate Similarity	NPD7871	Phase 2
0.7947	Intermediate Similarity	NPD6823	Phase 2
0.7943	Intermediate Similarity	NPD6959	Discontinued
0.7926	Intermediate Similarity	NPD7700	Phase 2
0.7926	Intermediate Similarity	NPD7699	Phase 2
0.7923	Intermediate Similarity	NPD8150	Discontinued
0.7921	Intermediate Similarity	NPD3818	Discontinued
0.7907	Intermediate Similarity	NPD7819	Suspended
0.7866	Intermediate Similarity	NPD2346	Discontinued
0.7865	Intermediate Similarity	NPD8320	Phase 1
0.7865	Intermediate Similarity	NPD8319	Approved
0.7846	Intermediate Similarity	NPD7874	Approved
0.7846	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4380	Phase 2
0.7806	Intermediate Similarity	NPD7801	Approved
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7766	Intermediate Similarity	NPD6534	Approved
0.7766	Intermediate Similarity	NPD6535	Approved
0.7722	Intermediate Similarity	NPD3751	Discontinued
0.7713	Intermediate Similarity	NPD6212	Phase 3
0.7713	Intermediate Similarity	NPD6213	Phase 3
0.7713	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6166	Phase 2
0.7705	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7473	Discontinued
0.7657	Intermediate Similarity	NPD5402	Approved
0.7657	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7228	Approved
0.76	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6232	Discontinued
0.7582	Intermediate Similarity	NPD5844	Phase 1
0.7572	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD1934	Approved
0.754	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5494	Approved
0.7471	Intermediate Similarity	NPD7458	Discontinued
0.7463	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5403	Approved
0.7443	Intermediate Similarity	NPD6801	Discontinued
0.7418	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7768	Phase 2
0.7416	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4628	Phase 3
0.7403	Intermediate Similarity	NPD3787	Discontinued
0.7394	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7411	Suspended
0.7366	Intermediate Similarity	NPD7240	Approved
0.7366	Intermediate Similarity	NPD7685	Pre-registration
0.7353	Intermediate Similarity	NPD6674	Discontinued
0.7341	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5401	Approved
0.731	Intermediate Similarity	NPD3750	Approved
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2801	Approved
0.7294	Intermediate Similarity	NPD1549	Phase 2
0.7286	Intermediate Similarity	NPD8059	Phase 3
0.7286	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7247	Intermediate Similarity	NPD37	Approved
0.7245	Intermediate Similarity	NPD8285	Discontinued
0.7241	Intermediate Similarity	NPD2532	Approved
0.7241	Intermediate Similarity	NPD2533	Approved
0.7241	Intermediate Similarity	NPD2534	Approved
0.7241	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6234	Discontinued
0.7235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7266	Discontinued
0.7235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6599	Discontinued
0.7222	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD4967	Phase 2
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7222	Intermediate Similarity	NPD4965	Approved
0.7219	Intermediate Similarity	NPD2799	Discontinued
0.7209	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1465	Phase 2
0.72	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1470	Approved
0.7176	Intermediate Similarity	NPD1551	Phase 2
0.7167	Intermediate Similarity	NPD3817	Phase 2
0.7164	Intermediate Similarity	NPD7584	Approved
0.7151	Intermediate Similarity	NPD6844	Discontinued
0.7151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2798	Approved
0.7088	Intermediate Similarity	NPD3749	Approved
0.7086	Intermediate Similarity	NPD6799	Approved
0.7086	Intermediate Similarity	NPD1511	Approved
0.7076	Intermediate Similarity	NPD2796	Approved
0.7052	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7045	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1933	Approved
0.7037	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3748	Approved
0.7018	Intermediate Similarity	NPD1510	Phase 2
0.7018	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD1512	Approved
0.7006	Intermediate Similarity	NPD6273	Approved
0.7005	Intermediate Similarity	NPD7930	Approved
0.7	Intermediate Similarity	NPD1607	Approved
0.6989	Remote Similarity	NPD7390	Discontinued
0.6981	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5408	Approved
0.6977	Remote Similarity	NPD5404	Approved
0.6977	Remote Similarity	NPD5406	Approved
0.6977	Remote Similarity	NPD6099	Approved
0.6977	Remote Similarity	NPD6100	Approved
0.6977	Remote Similarity	NPD5405	Approved
0.6973	Remote Similarity	NPD8127	Discontinued
0.6973	Remote Similarity	NPD7199	Phase 2
0.6968	Remote Similarity	NPD7177	Discontinued
0.6959	Remote Similarity	NPD7097	Phase 1
0.6941	Remote Similarity	NPD447	Suspended
0.6936	Remote Similarity	NPD2344	Approved
0.6936	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1091	Approved
0.6933	Remote Similarity	NPD1201	Approved
0.6931	Remote Similarity	NPD7680	Approved
0.6927	Remote Similarity	NPD1653	Approved
0.6905	Remote Similarity	NPD4625	Phase 3
0.69	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4060	Phase 1
0.6882	Remote Similarity	NPD1240	Approved
0.6878	Remote Similarity	NPD7799	Discontinued
0.6878	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1203	Approved
0.6866	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7985	Registered
0.6863	Remote Similarity	NPD7999	Approved
0.6859	Remote Similarity	NPD5953	Discontinued
0.6857	Remote Similarity	NPD2800	Approved
0.6845	Remote Similarity	NPD5710	Approved
0.6845	Remote Similarity	NPD5711	Approved
0.6842	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5762	Approved
0.6839	Remote Similarity	NPD5763	Approved
0.6821	Remote Similarity	NPD7033	Discontinued
0.6821	Remote Similarity	NPD4308	Phase 3
0.6818	Remote Similarity	NPD8166	Discontinued
0.6809	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2651	Approved
0.6796	Remote Similarity	NPD7585	Approved
0.6796	Remote Similarity	NPD2649	Approved
0.6782	Remote Similarity	NPD2438	Suspended
0.678	Remote Similarity	NPD2309	Approved
0.6778	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8404	Phase 2
0.6774	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD411	Approved
0.676	Remote Similarity	NPD4661	Approved
0.676	Remote Similarity	NPD4662	Approved
0.6754	Remote Similarity	NPD7286	Phase 2
0.6748	Remote Similarity	NPD7583	Approved
0.6744	Remote Similarity	NPD6355	Discontinued
0.6743	Remote Similarity	NPD1471	Phase 3
0.6742	Remote Similarity	NPD3300	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data