NPASS Compound

Structure

CID306168 OpenBabel06191716112D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.9657 2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3118 1.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4563 -0.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1481 0.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4891 2.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7820 1.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0351 -0.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0474 -0.5337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6948 0.5507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7351 1.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2531 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4891 0.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8718 3.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3241 1.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1473 0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 1.4417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4891 2.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1962 0.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1473 2.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7820 0.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1962 1.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4891 0.2009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8910 0.4540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8632 3.6695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4563 3.1681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 18 2 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 24 1 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 26 2 0 0 0 0 16 20 1 0 0 0 0 17 25 1 6 0 0 0 19 10 1 1 0 0 0 19 28 1 0 0 0 0 20 13 1 1 0 0 0 20 23 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 22 24 1 6 0 0 0 22 25 1 0 0 0 0 23 18 1 1 0 0 0 24 5 1 6 0 0 0 25 9 1 6 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.25
Volume:	419.919
LogP:	4.923
LogD:	4.254
LogS:	-5.888
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	5.639
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.81
MDCK Permeability:	2.7846452212543227e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.754
30% Bioavailability (F30%):	0.354

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	96.40612030029297%
Volume Distribution (VD):	2.959
Pgp-substrate:	3.655010461807251%

ADMET: Metabolism

CYP1A2-inhibitor:	0.519
CYP1A2-substrate:	0.634
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.763
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.842
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.56

ADMET: Excretion

Clearance (CL):	5.572
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.902
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.776
Carcinogencity:	0.111
Eye Corrosion:	0.004
Eye Irritation:	0.109
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC306168

Natural Product ID:	NPC306168
*Common Name:**	MDYSLOGZXCWLSL-CWPAWFJGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MDYSLOGZXCWLSL-CWPAWFJGSA-N
Standard InCHI:	InChI=1S/C25H34O3/c1-15(2)10-19-12-17(4)25(28-19)9-8-24(5)13-20-16(3)11-21(27)23(20)18(14-26)6-7-22(24)25/h6,10-11,14,17,19-20,22-23H,7-9,12-13H2,1-5H3/b18-6-/t17-,19-,20+,22+,23+,24+,25-/m0/s1
SMILES:	CC(=C[C@H]1C[C@H](C)[C@]2(CC[C@]3(C)C[C@@H]4C(=CC(=O)[C@@H]4C(=CC[C@@H]23)C=O)C)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2393052
PubChem CID:	12306827
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002882] Ophiobolane sesterterpenoids

*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
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395513]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO13275	Centaurea scabiosa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO12794	Hypericum pseudopetiolatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2613	Artemisia ordosica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5756	Amanita abrupta	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16542	Aloe rupestris	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119.2	Pseudomonas chlororaphis subsp. aureofaciens	Subspecies	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15571	Iphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11651	Parsonsia heterophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16867	Bursera permollis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13275	Centaurea scabiosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2990	Solenostemon scutellarioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	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
MIC	6

Activity Type	# Activity
Cell Line	2
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	55700.0	nM	PMID[494496]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	39500.0	nM	PMID[494496]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[494496]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[494496]
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC	>	100.0	ug.mL-1	PMID[494496]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[494496]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	>	100.0	ug.mL-1	PMID[494496]

☑ 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 NPC306168 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	245
0.1-0.2	1766
0.2-0.3	7918
0.3-0.4	16161
0.4-0.5	8664
0.5-0.6	5998
0.6-0.7	1790
0.7-0.8	131
0.8-0.85	8
0.85-0.9	13
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49946
0.8936	High Similarity	NPC25639
0.8889	High Similarity	NPC37816
0.883	High Similarity	NPC195192
0.883	High Similarity	NPC304738
0.8085	Intermediate Similarity	NPC229976
0.8043	Intermediate Similarity	NPC477710
0.7979	Intermediate Similarity	NPC290651
0.7979	Intermediate Similarity	NPC190442
0.7957	Intermediate Similarity	NPC41217
0.7872	Intermediate Similarity	NPC477711
0.7872	Intermediate Similarity	NPC2946
0.7857	Intermediate Similarity	NPC471610
0.7802	Intermediate Similarity	NPC238197
0.7791	Intermediate Similarity	NPC469678
0.7791	Intermediate Similarity	NPC475771
0.7791	Intermediate Similarity	NPC469669
0.7789	Intermediate Similarity	NPC221282
0.7674	Intermediate Similarity	NPC469691
0.7674	Intermediate Similarity	NPC167049
0.764	Intermediate Similarity	NPC469690
0.7634	Intermediate Similarity	NPC261253
0.7634	Intermediate Similarity	NPC470050
0.7634	Intermediate Similarity	NPC474045
0.7634	Intermediate Similarity	NPC470051
0.7609	Intermediate Similarity	NPC475100
0.7582	Intermediate Similarity	NPC20262
0.7582	Intermediate Similarity	NPC256750
0.7579	Intermediate Similarity	NPC170775
0.7576	Intermediate Similarity	NPC151488
0.7558	Intermediate Similarity	NPC92909
0.7558	Intermediate Similarity	NPC107783
0.7449	Intermediate Similarity	NPC90453
0.7447	Intermediate Similarity	NPC107787
0.7444	Intermediate Similarity	NPC469620
0.7444	Intermediate Similarity	NPC301769
0.7416	Intermediate Similarity	NPC53581
0.7416	Intermediate Similarity	NPC103987
0.74	Intermediate Similarity	NPC477949
0.7396	Intermediate Similarity	NPC477215
0.7396	Intermediate Similarity	NPC476388
0.7386	Intermediate Similarity	NPC251435
0.7379	Intermediate Similarity	NPC168575
0.7374	Intermediate Similarity	NPC474490
0.7368	Intermediate Similarity	NPC45957
0.7368	Intermediate Similarity	NPC471657
0.7363	Intermediate Similarity	NPC74673
0.7363	Intermediate Similarity	NPC276356
0.7363	Intermediate Similarity	NPC69271
0.7363	Intermediate Similarity	NPC47747
0.7363	Intermediate Similarity	NPC302426
0.734	Intermediate Similarity	NPC78089
0.734	Intermediate Similarity	NPC161957
0.734	Intermediate Similarity	NPC33570
0.734	Intermediate Similarity	NPC21471
0.7333	Intermediate Similarity	NPC228911
0.7333	Intermediate Similarity	NPC128276
0.732	Intermediate Similarity	NPC37607
0.732	Intermediate Similarity	NPC301969
0.7312	Intermediate Similarity	NPC215294
0.7312	Intermediate Similarity	NPC470046
0.7312	Intermediate Similarity	NPC470047
0.7308	Intermediate Similarity	NPC294259
0.7303	Intermediate Similarity	NPC215481
0.7303	Intermediate Similarity	NPC226242
0.7283	Intermediate Similarity	NPC471325
0.7264	Intermediate Similarity	NPC177064
0.7263	Intermediate Similarity	NPC469676
0.7255	Intermediate Similarity	NPC470906
0.7253	Intermediate Similarity	NPC32758
0.7253	Intermediate Similarity	NPC182550
0.7245	Intermediate Similarity	NPC284185
0.7234	Intermediate Similarity	NPC475796
0.7234	Intermediate Similarity	NPC115786
0.7222	Intermediate Similarity	NPC57744
0.7222	Intermediate Similarity	NPC122264
0.7216	Intermediate Similarity	NPC288699
0.7216	Intermediate Similarity	NPC232747
0.7209	Intermediate Similarity	NPC469677
0.7204	Intermediate Similarity	NPC35556
0.72	Intermediate Similarity	NPC67584
0.72	Intermediate Similarity	NPC476487
0.72	Intermediate Similarity	NPC476488
0.7191	Intermediate Similarity	NPC244166
0.7188	Intermediate Similarity	NPC478145
0.7188	Intermediate Similarity	NPC478144
0.7184	Intermediate Similarity	NPC475099
0.7184	Intermediate Similarity	NPC477950
0.7184	Intermediate Similarity	NPC310981
0.7174	Intermediate Similarity	NPC472470
0.7158	Intermediate Similarity	NPC96621
0.7158	Intermediate Similarity	NPC470048
0.7158	Intermediate Similarity	NPC235792
0.7158	Intermediate Similarity	NPC245434
0.7157	Intermediate Similarity	NPC252295
0.7143	Intermediate Similarity	NPC222210
0.7143	Intermediate Similarity	NPC63445
0.7143	Intermediate Similarity	NPC299235
0.7143	Intermediate Similarity	NPC474056
0.7143	Intermediate Similarity	NPC253144
0.7129	Intermediate Similarity	NPC322063
0.7129	Intermediate Similarity	NPC213078
0.7129	Intermediate Similarity	NPC121036
0.7129	Intermediate Similarity	NPC472674
0.7128	Intermediate Similarity	NPC39588
0.7128	Intermediate Similarity	NPC193198
0.7128	Intermediate Similarity	NPC108045
0.7128	Intermediate Similarity	NPC475622
0.7113	Intermediate Similarity	NPC469628
0.7113	Intermediate Similarity	NPC469631
0.7113	Intermediate Similarity	NPC28227
0.7113	Intermediate Similarity	NPC469653
0.7113	Intermediate Similarity	NPC226863
0.7113	Intermediate Similarity	NPC91248
0.7113	Intermediate Similarity	NPC475906
0.7113	Intermediate Similarity	NPC471047
0.71	Intermediate Similarity	NPC477131
0.71	Intermediate Similarity	NPC167219
0.7097	Intermediate Similarity	NPC35089
0.7097	Intermediate Similarity	NPC10276
0.7097	Intermediate Similarity	NPC42470
0.7093	Intermediate Similarity	NPC469688
0.7093	Intermediate Similarity	NPC469679
0.7083	Intermediate Similarity	NPC64153
0.7083	Intermediate Similarity	NPC195640
0.7083	Intermediate Similarity	NPC279859
0.7083	Intermediate Similarity	NPC38576
0.7075	Intermediate Similarity	NPC60681
0.7071	Intermediate Similarity	NPC74103
0.7071	Intermediate Similarity	NPC123177
0.7071	Intermediate Similarity	NPC150978
0.7071	Intermediate Similarity	NPC70595
0.7065	Intermediate Similarity	NPC261125
0.7065	Intermediate Similarity	NPC178277
0.7065	Intermediate Similarity	NPC181195
0.7059	Intermediate Similarity	NPC161493
0.7059	Intermediate Similarity	NPC213947
0.7059	Intermediate Similarity	NPC108475
0.7059	Intermediate Similarity	NPC170143
0.7053	Intermediate Similarity	NPC156485
0.7053	Intermediate Similarity	NPC474359
0.7048	Intermediate Similarity	NPC176883
0.7041	Intermediate Similarity	NPC123912
0.7041	Intermediate Similarity	NPC285982
0.7041	Intermediate Similarity	NPC4986
0.7033	Intermediate Similarity	NPC65603
0.7033	Intermediate Similarity	NPC276769
0.7033	Intermediate Similarity	NPC15975
0.7033	Intermediate Similarity	NPC195785
0.7033	Intermediate Similarity	NPC86917
0.703	Intermediate Similarity	NPC470978
0.703	Intermediate Similarity	NPC52044
0.703	Intermediate Similarity	NPC280877
0.703	Intermediate Similarity	NPC470974
0.703	Intermediate Similarity	NPC33473
0.7021	Intermediate Similarity	NPC173609
0.7021	Intermediate Similarity	NPC145963
0.7011	Intermediate Similarity	NPC22301
0.7	Intermediate Similarity	NPC475700
0.7	Intermediate Similarity	NPC250575
0.7	Intermediate Similarity	NPC477361
0.7	Intermediate Similarity	NPC202824
0.699	Remote Similarity	NPC109556
0.699	Remote Similarity	NPC222011
0.6989	Remote Similarity	NPC290508
0.6989	Remote Similarity	NPC73052
0.6989	Remote Similarity	NPC6823
0.6989	Remote Similarity	NPC293418
0.6981	Remote Similarity	NPC189616
0.6981	Remote Similarity	NPC472868
0.6979	Remote Similarity	NPC323765
0.6979	Remote Similarity	NPC189311
0.6979	Remote Similarity	NPC177932
0.6979	Remote Similarity	NPC125290
0.6972	Remote Similarity	NPC179642
0.6961	Remote Similarity	NPC24956
0.6961	Remote Similarity	NPC477354
0.6961	Remote Similarity	NPC18019
0.6961	Remote Similarity	NPC307164
0.6957	Remote Similarity	NPC207186
0.6957	Remote Similarity	NPC471220
0.6957	Remote Similarity	NPC253749
0.6952	Remote Similarity	NPC118405
0.6947	Remote Similarity	NPC472473
0.6947	Remote Similarity	NPC65350
0.6947	Remote Similarity	NPC245665
0.6947	Remote Similarity	NPC54468
0.6947	Remote Similarity	NPC475947
0.6944	Remote Similarity	NPC61411
0.6939	Remote Similarity	NPC224652
0.6931	Remote Similarity	NPC294266
0.6931	Remote Similarity	NPC127019
0.6931	Remote Similarity	NPC262133
0.6931	Remote Similarity	NPC53685
0.6931	Remote Similarity	NPC470013
0.6931	Remote Similarity	NPC323008
0.6931	Remote Similarity	NPC148463
0.6931	Remote Similarity	NPC198853
0.6931	Remote Similarity	NPC470010
0.6923	Remote Similarity	NPC473223

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 NPC306168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	2415
0.2-0.3	4257
0.3-0.4	1619
0.4-0.5	334
0.5-0.6	223
0.6-0.7	76
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7143	Intermediate Similarity	NPD5785	Approved
0.7113	Intermediate Similarity	NPD6903	Approved
0.7083	Intermediate Similarity	NPD5330	Approved
0.7083	Intermediate Similarity	NPD7334	Approved
0.7083	Intermediate Similarity	NPD7146	Approved
0.7083	Intermediate Similarity	NPD6684	Approved
0.7083	Intermediate Similarity	NPD7521	Approved
0.7083	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD1695	Approved
0.6979	Remote Similarity	NPD1694	Approved
0.6947	Remote Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5693	Phase 1
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5209	Approved
0.6842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5207	Approved
0.6701	Remote Similarity	NPD3665	Phase 1
0.6701	Remote Similarity	NPD3133	Approved
0.6701	Remote Similarity	NPD3666	Approved
0.67	Remote Similarity	NPD6080	Approved
0.67	Remote Similarity	NPD6673	Approved
0.67	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6633	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD5363	Approved
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6001	Approved
0.66	Remote Similarity	NPD5737	Approved
0.66	Remote Similarity	NPD6672	Approved
0.66	Remote Similarity	NPD5208	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD6050	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6566	Remote Similarity	NPD6098	Approved
0.6538	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD6051	Approved
0.6535	Remote Similarity	NPD4753	Phase 2
0.6531	Remote Similarity	NPD4197	Approved
0.6505	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD5692	Phase 3
0.6455	Remote Similarity	NPD6008	Approved
0.6442	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD4788	Approved
0.6408	Remote Similarity	NPD6079	Approved
0.6408	Remote Similarity	NPD5694	Approved
0.64	Remote Similarity	NPD4688	Approved
0.64	Remote Similarity	NPD4138	Approved
0.64	Remote Similarity	NPD5280	Approved
0.64	Remote Similarity	NPD4694	Approved
0.64	Remote Similarity	NPD5279	Phase 3
0.64	Remote Similarity	NPD4689	Approved
0.64	Remote Similarity	NPD5786	Approved
0.64	Remote Similarity	NPD4690	Approved
0.64	Remote Similarity	NPD4693	Phase 3
0.64	Remote Similarity	NPD5205	Approved
0.6392	Remote Similarity	NPD5369	Approved
0.6392	Remote Similarity	NPD4790	Discontinued
0.6381	Remote Similarity	NPD4629	Approved
0.6381	Remote Similarity	NPD5210	Approved
0.6373	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6355	Remote Similarity	NPD7638	Approved
0.6355	Remote Similarity	NPD5696	Approved
0.6346	Remote Similarity	NPD6399	Phase 3
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.6339	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD5211	Phase 2
0.6327	Remote Similarity	NPD6435	Approved
0.6327	Remote Similarity	NPD4270	Approved
0.6327	Remote Similarity	NPD4269	Approved
0.6321	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD6650	Approved
0.6316	Remote Similarity	NPD6649	Approved
0.6306	Remote Similarity	NPD5739	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6283	Remote Similarity	NPD6373	Approved
0.6283	Remote Similarity	NPD6372	Approved
0.6277	Remote Similarity	NPD8039	Approved
0.6275	Remote Similarity	NPD4518	Approved
0.6273	Remote Similarity	NPD6052	Approved
0.6263	Remote Similarity	NPD5332	Approved
0.6263	Remote Similarity	NPD5331	Approved
0.6263	Remote Similarity	NPD7154	Phase 3
0.6262	Remote Similarity	NPD4755	Approved
0.6261	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD5697	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.6238	Remote Similarity	NPD3618	Phase 1
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6195	Remote Similarity	NPD6011	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6186	Remote Similarity	NPD4195	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.618	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7507	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6174	Remote Similarity	NPD6617	Approved
0.6162	Remote Similarity	NPD3667	Approved
0.6154	Remote Similarity	NPD4096	Approved
0.6148	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4700	Approved
0.614	Remote Similarity	NPD6014	Approved
0.614	Remote Similarity	NPD6013	Approved
0.614	Remote Similarity	NPD6012	Approved
0.6139	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5175	Approved
0.6126	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD4820	Approved
0.6122	Remote Similarity	NPD4252	Approved
0.6122	Remote Similarity	NPD4819	Approved
0.6122	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4821	Approved
0.6122	Remote Similarity	NPD5368	Approved
0.6122	Remote Similarity	NPD4822	Approved
0.6121	Remote Similarity	NPD6882	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD5701	Approved
0.6095	Remote Similarity	NPD5284	Approved
0.6095	Remote Similarity	NPD5281	Approved
0.6078	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4623	Approved
0.6078	Remote Similarity	NPD4519	Discontinued
0.6075	Remote Similarity	NPD5654	Approved
0.604	Remote Similarity	NPD3668	Phase 3
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6054	Approved
0.6032	Remote Similarity	NPD7319	Approved
0.6022	Remote Similarity	NPD4747	Approved
0.6022	Remote Similarity	NPD4691	Approved
0.6019	Remote Similarity	NPD5222	Approved
0.6019	Remote Similarity	NPD4250	Approved
0.6019	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5221	Approved
0.6019	Remote Similarity	NPD4251	Approved
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5733	Approved
0.5982	Remote Similarity	NPD4754	Approved
0.5981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7900	Approved
0.5965	Remote Similarity	NPD6614	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5963	Remote Similarity	NPD5173	Approved
0.5963	Remote Similarity	NPD5959	Approved
0.5957	Remote Similarity	NPD5276	Approved
0.5935	Remote Similarity	NPD6370	Approved
0.5934	Remote Similarity	NPD7331	Phase 2
0.5922	Remote Similarity	NPD4249	Approved
0.5918	Remote Similarity	NPD4271	Approved
0.5918	Remote Similarity	NPD4268	Approved
0.5914	Remote Similarity	NPD4137	Phase 3
0.5913	Remote Similarity	NPD4729	Approved
0.5913	Remote Similarity	NPD5128	Approved
0.5913	Remote Similarity	NPD4730	Approved
0.5913	Remote Similarity	NPD6686	Approved
0.5909	Remote Similarity	NPD4225	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.59	Remote Similarity	NPD4692	Approved
0.59	Remote Similarity	NPD4139	Approved
0.5888	Remote Similarity	NPD5133	Approved
0.5877	Remote Similarity	NPD4767	Approved
0.5877	Remote Similarity	NPD4768	Approved
0.5873	Remote Similarity	NPD7078	Approved
0.5868	Remote Similarity	NPD6335	Approved
0.5865	Remote Similarity	NPD3573	Approved
0.5854	Remote Similarity	NPD6015	Approved
0.5854	Remote Similarity	NPD6016	Approved
0.5854	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6698	Approved
0.5849	Remote Similarity	NPD46	Approved
0.584	Remote Similarity	NPD7492	Approved
0.5833	Remote Similarity	NPD6924	Approved
0.5833	Remote Similarity	NPD6926	Approved
0.5833	Remote Similarity	NPD6274	Approved
0.5833	Remote Similarity	NPD4687	Approved
0.5833	Remote Similarity	NPD7748	Approved
0.5833	Remote Similarity	NPD4058	Approved
0.5824	Remote Similarity	NPD7341	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