NPASS Compound

Structure

CID203751 OpenBabel06191715592D 41 46 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 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 0.8660 1.5000 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 -0.0000 -3.0000 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 -1.7321 -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 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 2 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 0.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 1.7321 -0.0000 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 9.5263 0.5000 0.0000 C 0 0 2 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 17 1 0 0 0 0 6 22 2 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 11 24 1 0 0 0 0 12 21 1 0 0 0 0 12 23 1 0 0 0 0 14 2 1 1 0 0 0 14 28 1 0 0 0 0 14 38 1 0 0 0 0 15 3 1 1 0 0 0 15 31 1 0 0 0 0 15 39 1 0 0 0 0 16 25 2 0 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 18 27 2 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 32 1 0 0 0 0 20 28 1 0 0 0 0 20 33 1 1 0 0 0 21 31 1 0 0 0 0 21 34 1 1 0 0 0 22 26 1 0 0 0 0 22 40 1 0 0 0 0 23 39 1 0 0 0 0 23 40 1 1 0 0 0 24 38 1 0 0 0 0 24 41 1 1 0 0 0 25 27 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 28 35 1 6 0 0 0 29 36 2 0 0 0 0 30 37 2 0 0 0 0 31 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.2
Volume:	554.931
LogP:	4.194
LogD:	2.883
LogS:	-6.623
# Rotatable Bonds:	4
TPSA:	151.98
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	4.661
Fsp3:	0.419
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.368
MDCK Permeability:	4.2671501432778314e-05
Pgp-inhibitor:	0.592
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.728

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	97.4782943725586%
Volume Distribution (VD):	0.837
Pgp-substrate:	1.8664151430130005%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.695
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.706
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.282
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	8.286
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.516
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.891
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.542
Carcinogencity:	0.96
Eye Corrosion:	0.003
Eye Irritation:	0.197
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC203751

Natural Product ID:	NPC203751
*Common Name:**	Landomycin O
IUPAC Name:	8-[(2S,4R,5S,6R)-5-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-3-methylbenzo[a]anthracene-7,12-dione
Synonyms:	Landomycin O
Standard InCHIKey:	PALOVKKTEPSBNX-UXLRNTTNSA-N
Standard InCHI:	InChI=1S/C31H32O10/c1-13-9-16-7-8-18-27(25(16)19(32)10-13)30(37)17-5-4-6-22(26(17)29(18)36)40-23-12-21(34)31(15(3)39-23)41-24-11-20(33)28(35)14(2)38-24/h4-10,14-15,20-21,23-24,28,31-35H,11-12H2,1-3H3/t14-,15-,20-,21-,23+,24+,28-,31-/m1/s1
SMILES:	O[C@@H]1C[C@@H](O[C@@H]([C@H]1O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O)C)Oc1cccc2c1C(=O)c1ccc3c(c1C2=O)c(O)cc(c3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668343
PubChem CID:	53317507
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003415] Angucyclines

*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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3550.0	nM	PMID[465711]

☑ 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 NPC203751 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	420
0.1-0.2	1575
0.2-0.3	3266
0.3-0.4	7912
0.4-0.5	9662
0.5-0.6	5732
0.6-0.7	5938
0.7-0.8	6630
0.8-0.85	1289
0.85-0.9	203
0.9-0.95	62
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC289876
0.9877	High Similarity	NPC102053
0.9758	High Similarity	NPC58538
0.9755	High Similarity	NPC85368
0.9699	High Similarity	NPC85316
0.9699	High Similarity	NPC197357
0.9583	High Similarity	NPC224557
0.9583	High Similarity	NPC292706
0.9527	High Similarity	NPC87583
0.9521	High Similarity	NPC114257
0.9521	High Similarity	NPC277710
0.9521	High Similarity	NPC153578
0.9521	High Similarity	NPC299149
0.9509	High Similarity	NPC63470
0.9503	High Similarity	NPC146837
0.9503	High Similarity	NPC101116
0.9503	High Similarity	NPC212099
0.9503	High Similarity	NPC278329
0.9458	High Similarity	NPC186800
0.9458	High Similarity	NPC470667
0.9401	High Similarity	NPC46958
0.9401	High Similarity	NPC475246
0.9387	High Similarity	NPC178281
0.9349	High Similarity	NPC477860
0.9349	High Similarity	NPC475161
0.9341	High Similarity	NPC3718
0.9333	High Similarity	NPC246274
0.9286	High Similarity	NPC170018
0.9286	High Similarity	NPC92403
0.9286	High Similarity	NPC66820
0.9286	High Similarity	NPC76112
0.9281	High Similarity	NPC199357
0.9264	High Similarity	NPC216752
0.9226	High Similarity	NPC223735
0.9226	High Similarity	NPC307754
0.9222	High Similarity	NPC315619
0.9222	High Similarity	NPC76128
0.9222	High Similarity	NPC5029
0.9222	High Similarity	NPC30432
0.9222	High Similarity	NPC111536
0.9222	High Similarity	NPC271385
0.9198	High Similarity	NPC53139
0.9191	High Similarity	NPC205721
0.9167	High Similarity	NPC213052
0.9152	High Similarity	NPC478020
0.9152	High Similarity	NPC478022
0.9146	High Similarity	NPC187934
0.9146	High Similarity	NPC97637
0.9133	High Similarity	NPC105591
0.9112	High Similarity	NPC68381
0.9102	High Similarity	NPC222455
0.9075	High Similarity	NPC241847
0.9059	High Similarity	NPC475233
0.9059	High Similarity	NPC198893
0.9059	High Similarity	NPC232818
0.9059	High Similarity	NPC314489
0.9	High Similarity	NPC63105
0.8988	High Similarity	NPC259905
0.8982	High Similarity	NPC178851
0.8977	High Similarity	NPC264302
0.8976	High Similarity	NPC17432
0.8966	High Similarity	NPC475352
0.8966	High Similarity	NPC221140
0.8966	High Similarity	NPC229817
0.8966	High Similarity	NPC473686
0.8966	High Similarity	NPC475220
0.896	High Similarity	NPC473717
0.896	High Similarity	NPC476203
0.896	High Similarity	NPC313452
0.896	High Similarity	NPC293227
0.896	High Similarity	NPC473631
0.896	High Similarity	NPC475662
0.8953	High Similarity	NPC245059
0.8953	High Similarity	NPC212290
0.8953	High Similarity	NPC84494
0.8941	High Similarity	NPC98776
0.8935	High Similarity	NPC52598
0.8935	High Similarity	NPC478021
0.8935	High Similarity	NPC298778
0.8922	High Similarity	NPC99216
0.892	High Similarity	NPC314672
0.8902	High Similarity	NPC470452
0.8902	High Similarity	NPC470448
0.8902	High Similarity	NPC208651
0.8902	High Similarity	NPC206641
0.8902	High Similarity	NPC470453
0.8902	High Similarity	NPC315221
0.8902	High Similarity	NPC164047
0.8895	High Similarity	NPC47191
0.8889	High Similarity	NPC146803
0.8882	High Similarity	NPC294501
0.8882	High Similarity	NPC183441
0.8851	High Similarity	NPC478001
0.8841	High Similarity	NPC283480
0.8841	High Similarity	NPC148323
0.883	High Similarity	NPC472054
0.883	High Similarity	NPC168789
0.8817	High Similarity	NPC103633
0.8795	High Similarity	NPC328093
0.8788	High Similarity	NPC177742
0.878	High Similarity	NPC192219
0.878	High Similarity	NPC3449
0.878	High Similarity	NPC174599
0.878	High Similarity	NPC82190
0.8779	High Similarity	NPC470454
0.8779	High Similarity	NPC474345
0.8779	High Similarity	NPC199533
0.8772	High Similarity	NPC478002
0.8765	High Similarity	NPC473202
0.8765	High Similarity	NPC175477
0.875	High Similarity	NPC257566
0.875	High Similarity	NPC124155
0.8743	High Similarity	NPC73148
0.8736	High Similarity	NPC72783
0.8728	High Similarity	NPC176246
0.872	High Similarity	NPC205172
0.872	High Similarity	NPC474621
0.872	High Similarity	NPC474622
0.872	High Similarity	NPC209393
0.8715	High Similarity	NPC470199
0.8715	High Similarity	NPC314459
0.8713	High Similarity	NPC76047
0.8713	High Similarity	NPC313304
0.8701	High Similarity	NPC65489
0.8698	High Similarity	NPC297404
0.8698	High Similarity	NPC11608
0.8698	High Similarity	NPC478026
0.8693	High Similarity	NPC231254
0.869	High Similarity	NPC44947
0.869	High Similarity	NPC190450
0.8683	High Similarity	NPC472320
0.8678	High Similarity	NPC478000
0.8671	High Similarity	NPC70862
0.8659	High Similarity	NPC474533
0.8659	High Similarity	NPC474534
0.8655	High Similarity	NPC470206
0.8655	High Similarity	NPC470207
0.8652	High Similarity	NPC473618
0.8647	High Similarity	NPC178173
0.8647	High Similarity	NPC70441
0.8636	High Similarity	NPC321916
0.8636	High Similarity	NPC132111
0.8631	High Similarity	NPC303913
0.8631	High Similarity	NPC47923
0.8631	High Similarity	NPC472261
0.8631	High Similarity	NPC132737
0.8623	High Similarity	NPC324736
0.8619	High Similarity	NPC470195
0.8619	High Similarity	NPC470196
0.8619	High Similarity	NPC470193
0.8619	High Similarity	NPC470200
0.8619	High Similarity	NPC470194
0.8619	High Similarity	NPC470197
0.8619	High Similarity	NPC316274
0.8619	High Similarity	NPC282474
0.8619	High Similarity	NPC470198
0.8613	High Similarity	NPC470336
0.8613	High Similarity	NPC208668
0.8613	High Similarity	NPC470335
0.8613	High Similarity	NPC154986
0.8613	High Similarity	NPC65118
0.8605	High Similarity	NPC150767
0.8605	High Similarity	NPC78734
0.8596	High Similarity	NPC298847
0.8596	High Similarity	NPC179947
0.8596	High Similarity	NPC470341
0.8596	High Similarity	NPC234497
0.8596	High Similarity	NPC472058
0.8596	High Similarity	NPC249977
0.8596	High Similarity	NPC105414
0.8596	High Similarity	NPC324522
0.8588	High Similarity	NPC75574
0.8588	High Similarity	NPC318119
0.858	High Similarity	NPC472876
0.858	High Similarity	NPC208797
0.858	High Similarity	NPC61594
0.858	High Similarity	NPC15374
0.858	High Similarity	NPC259834
0.858	High Similarity	NPC53680
0.858	High Similarity	NPC56735
0.8579	High Similarity	NPC131405
0.8571	High Similarity	NPC267549
0.8571	High Similarity	NPC271479
0.8571	High Similarity	NPC142860
0.8571	High Similarity	NPC246469
0.8571	High Similarity	NPC271270
0.8571	High Similarity	NPC97285
0.8571	High Similarity	NPC472387
0.8564	High Similarity	NPC316412
0.8564	High Similarity	NPC315351
0.8563	High Similarity	NPC19056
0.8563	High Similarity	NPC470583
0.8563	High Similarity	NPC193377
0.8563	High Similarity	NPC23817
0.8556	High Similarity	NPC48474
0.8555	High Similarity	NPC270027
0.8555	High Similarity	NPC256760
0.8555	High Similarity	NPC67134
0.8555	High Similarity	NPC47140
0.8554	High Similarity	NPC266469

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 NPC203751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	902
0.2-0.3	1650
0.3-0.4	2640
0.4-0.5	2060
0.5-0.6	1010
0.6-0.7	355
0.7-0.8	115
0.8-0.85	40
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD8313	Approved
0.9286	High Similarity	NPD8312	Approved
0.8914	High Similarity	NPD7879	Clinical (unspecified phase)
0.8631	High Similarity	NPD6959	Discontinued
0.8547	High Similarity	NPD7804	Clinical (unspecified phase)
0.8506	High Similarity	NPD6559	Discontinued
0.8497	Intermediate Similarity	NPD7074	Phase 3
0.8483	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.847	Intermediate Similarity	NPD6779	Approved
0.847	Intermediate Similarity	NPD6780	Approved
0.847	Intermediate Similarity	NPD6777	Approved
0.847	Intermediate Similarity	NPD6782	Approved
0.847	Intermediate Similarity	NPD6778	Approved
0.847	Intermediate Similarity	NPD6781	Approved
0.847	Intermediate Similarity	NPD6776	Approved
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7054	Approved
0.8432	Intermediate Similarity	NPD7698	Approved
0.8432	Intermediate Similarity	NPD7696	Phase 3
0.8432	Intermediate Similarity	NPD7435	Discontinued
0.8432	Intermediate Similarity	NPD7697	Approved
0.8404	Intermediate Similarity	NPD8151	Discontinued
0.8391	Intermediate Similarity	NPD7472	Approved
0.8387	Intermediate Similarity	NPD7871	Phase 2
0.8387	Intermediate Similarity	NPD7870	Phase 2
0.8351	Intermediate Similarity	NPD7701	Phase 2
0.8295	Intermediate Similarity	NPD7251	Discontinued
0.8274	Intermediate Similarity	NPD8455	Phase 2
0.8261	Intermediate Similarity	NPD7699	Phase 2
0.8261	Intermediate Similarity	NPD7700	Phase 2
0.8253	Intermediate Similarity	NPD3226	Approved
0.8249	Intermediate Similarity	NPD7808	Phase 3
0.8239	Intermediate Similarity	NPD6797	Phase 2
0.822	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD7783	Phase 2
0.8218	Intermediate Similarity	NPD7473	Discontinued
0.8197	Intermediate Similarity	NPD6535	Approved
0.8197	Intermediate Similarity	NPD6534	Approved
0.8182	Intermediate Similarity	NPD6823	Phase 2
0.8171	Intermediate Similarity	NPD3818	Discontinued
0.8168	Intermediate Similarity	NPD7874	Approved
0.8168	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD6166	Phase 2
0.8161	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6232	Discontinued
0.8142	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD6212	Phase 3
0.8142	Intermediate Similarity	NPD6213	Phase 3
0.8125	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD7801	Approved
0.8095	Intermediate Similarity	NPD8320	Phase 1
0.8095	Intermediate Similarity	NPD8319	Approved
0.8095	Intermediate Similarity	NPD4380	Phase 2
0.8068	Intermediate Similarity	NPD3751	Discontinued
0.8059	Intermediate Similarity	NPD7819	Suspended
0.8023	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8150	Discontinued
0.7955	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3787	Discontinued
0.7929	Intermediate Similarity	NPD7458	Discontinued
0.7929	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2346	Discontinued
0.7861	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7411	Suspended
0.7833	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD7228	Approved
0.7759	Intermediate Similarity	NPD7768	Phase 2
0.7727	Intermediate Similarity	NPD5494	Approved
0.7701	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6801	Discontinued
0.7665	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3749	Approved
0.7605	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD8059	Phase 3
0.7569	Intermediate Similarity	NPD7177	Discontinued
0.7545	Intermediate Similarity	NPD1549	Phase 2
0.7543	Intermediate Similarity	NPD1465	Phase 2
0.7543	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD6674	Discontinued
0.7487	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6599	Discontinued
0.7461	Intermediate Similarity	NPD8285	Discontinued
0.7458	Intermediate Similarity	NPD3882	Suspended
0.7456	Intermediate Similarity	NPD7003	Approved
0.7425	Intermediate Similarity	NPD5404	Approved
0.7425	Intermediate Similarity	NPD5406	Approved
0.7425	Intermediate Similarity	NPD5405	Approved
0.7425	Intermediate Similarity	NPD5408	Approved
0.7405	Intermediate Similarity	NPD7240	Approved
0.7401	Intermediate Similarity	NPD3817	Phase 2
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7386	Intermediate Similarity	NPD37	Approved
0.7384	Intermediate Similarity	NPD5401	Approved
0.7381	Intermediate Similarity	NPD2344	Approved
0.7374	Intermediate Similarity	NPD7584	Approved
0.7374	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD4966	Approved
0.736	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1470	Approved
0.7326	Intermediate Similarity	NPD1511	Approved
0.7326	Intermediate Similarity	NPD6799	Approved
0.7321	Intermediate Similarity	NPD2796	Approved
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.7317	Intermediate Similarity	NPD2313	Discontinued
0.7278	Intermediate Similarity	NPD7266	Discontinued
0.7262	Intermediate Similarity	NPD2799	Discontinued
0.7262	Intermediate Similarity	NPD1510	Phase 2
0.7251	Intermediate Similarity	NPD3750	Approved
0.7246	Intermediate Similarity	NPD1607	Approved
0.7241	Intermediate Similarity	NPD1512	Approved
0.7241	Intermediate Similarity	NPD6273	Approved
0.7225	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7213	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2309	Approved
0.7206	Intermediate Similarity	NPD7930	Approved
0.7202	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6844	Discontinued
0.7189	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2798	Approved
0.7176	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1240	Approved
0.712	Intermediate Similarity	NPD3926	Phase 2
0.7104	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD1933	Approved
0.7081	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1201	Approved
0.7074	Intermediate Similarity	NPD5953	Discontinued
0.7071	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5711	Approved
0.7065	Intermediate Similarity	NPD5710	Approved
0.7065	Intermediate Similarity	NPD7229	Phase 3
0.7065	Intermediate Similarity	NPD7999	Approved
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7056	Intermediate Similarity	NPD5761	Phase 2
0.7056	Intermediate Similarity	NPD5760	Phase 2
0.705	Intermediate Similarity	NPD7680	Approved
0.7048	Intermediate Similarity	NPD4625	Phase 3
0.702	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD920	Approved
0.7005	Intermediate Similarity	NPD7799	Discontinued
0.6995	Remote Similarity	NPD7585	Approved
0.6994	Remote Similarity	NPD2800	Approved
0.6982	Remote Similarity	NPD447	Suspended
0.6977	Remote Similarity	NPD1471	Phase 3
0.6975	Remote Similarity	NPD1091	Approved
0.6968	Remote Similarity	NPD7286	Phase 2
0.6966	Remote Similarity	NPD1653	Approved
0.6959	Remote Similarity	NPD3748	Approved
0.6946	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7583	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6919	Remote Similarity	NPD2438	Suspended
0.6919	Remote Similarity	NPD1247	Approved
0.6914	Remote Similarity	NPD6190	Approved
0.6909	Remote Similarity	NPD1203	Approved
0.6905	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3764	Approved
0.6905	Remote Similarity	NPD6798	Discontinued
0.6902	Remote Similarity	NPD919	Approved
0.6893	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5762	Approved
0.6879	Remote Similarity	NPD5763	Approved
0.686	Remote Similarity	NPD4308	Phase 3

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