NPASS Compound

Structure

NPC42630 OpenBabel07101719122D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.2247 -2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 1.7321 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 3.4641 -0.0000 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 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 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 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 1 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 0.8660 0.5000 0.0000 C 0 0 1 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 7 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 18 4 1 6 0 0 0 18 21 1 0 0 0 0 19 5 1 1 0 0 0 20 6 1 1 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.26
Volume:	334.961
LogP:	5.95
LogD:	4.483
LogS:	-5.396
# Rotatable Bonds:	1
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	4.307
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.602
MDCK Permeability:	1.7374984963680618e-05
Pgp-inhibitor:	0.752
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.118
30% Bioavailability (F30%):	0.18

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	95.0233154296875%
Volume Distribution (VD):	1.371
Pgp-substrate:	6.192986488342285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.678
CYP2C19-inhibitor:	0.191
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.558
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.692

ADMET: Excretion

Clearance (CL):	8.712
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.632
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.612
Skin Sensitization:	0.804
Carcinogencity:	0.269
Eye Corrosion:	0.964
Eye Irritation:	0.85
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC42630

Natural Product ID:	NPC42630
*Common Name:**	13-Epimanoyl Oxide
IUPAC Name:	(3S,4aR,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene
Synonyms:	13-Epimanoyl Oxide
Standard InCHIKey:	IGGWKHQYMAJOHK-GRLGQGAKSA-N
Standard InCHI:	InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18+,19-,20+/m0/s1
SMILES:	C=C[C@]1(C)CC[C@H]2[C@@](O1)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496057
PubChem CID:	2721426
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33340	picea glehni	Species	Pinaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[10869208]

☑ 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
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[469778]
NPT2	Others	Unspecified		Inhibition	=	4.3	%	PMID[469778]
NPT2	Others	Unspecified		Inhibition	=	35.9	%	PMID[469778]
NPT2	Others	Unspecified		Inhibition	=	70.4	%	PMID[469778]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[469778]

☑ 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 NPC42630 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	314
0.1-0.2	2893
0.2-0.3	11541
0.3-0.4	15046
0.4-0.5	6511
0.5-0.6	5050
0.6-0.7	1251
0.7-0.8	75
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC139785
0.8714	High Similarity	NPC198473
0.8592	High Similarity	NPC169994
0.8472	Intermediate Similarity	NPC137587
0.8333	Intermediate Similarity	NPC470750
0.8133	Intermediate Similarity	NPC48673
0.8133	Intermediate Similarity	NPC20096
0.8088	Intermediate Similarity	NPC117607
0.8088	Intermediate Similarity	NPC101307
0.8088	Intermediate Similarity	NPC88454
0.8082	Intermediate Similarity	NPC470751
0.806	Intermediate Similarity	NPC64123
0.7971	Intermediate Similarity	NPC2648
0.7857	Intermediate Similarity	NPC210323
0.7722	Intermediate Similarity	NPC477578
0.7714	Intermediate Similarity	NPC94192
0.7612	Intermediate Similarity	NPC41160
0.7606	Intermediate Similarity	NPC476431
0.7536	Intermediate Similarity	NPC474768
0.7468	Intermediate Similarity	NPC470558
0.7467	Intermediate Similarity	NPC470766
0.7432	Intermediate Similarity	NPC162164
0.7424	Intermediate Similarity	NPC189290
0.7424	Intermediate Similarity	NPC474769
0.7403	Intermediate Similarity	NPC476367
0.7403	Intermediate Similarity	NPC72755
0.7375	Intermediate Similarity	NPC15534
0.7375	Intermediate Similarity	NPC470077
0.7368	Intermediate Similarity	NPC474230
0.7361	Intermediate Similarity	NPC9942
0.7349	Intermediate Similarity	NPC59682
0.7342	Intermediate Similarity	NPC155521
0.7324	Intermediate Similarity	NPC474477
0.7297	Intermediate Similarity	NPC182717
0.7262	Intermediate Similarity	NPC474249
0.7262	Intermediate Similarity	NPC261990
0.7237	Intermediate Similarity	NPC104806
0.7237	Intermediate Similarity	NPC474231
0.7237	Intermediate Similarity	NPC470749
0.7222	Intermediate Similarity	NPC476945
0.7215	Intermediate Similarity	NPC70927
0.72	Intermediate Similarity	NPC201048
0.72	Intermediate Similarity	NPC476366
0.72	Intermediate Similarity	NPC38426
0.7183	Intermediate Similarity	NPC279434
0.7183	Intermediate Similarity	NPC476406
0.7176	Intermediate Similarity	NPC289361
0.7162	Intermediate Similarity	NPC110799
0.7162	Intermediate Similarity	NPC167706
0.7143	Intermediate Similarity	NPC470758
0.7143	Intermediate Similarity	NPC470711
0.7125	Intermediate Similarity	NPC470049
0.7125	Intermediate Similarity	NPC304285
0.7121	Intermediate Similarity	NPC39068
0.7121	Intermediate Similarity	NPC264779
0.7089	Intermediate Similarity	NPC269791
0.7073	Intermediate Similarity	NPC474013
0.7073	Intermediate Similarity	NPC157257
0.7073	Intermediate Similarity	NPC274448
0.7073	Intermediate Similarity	NPC164424
0.7059	Intermediate Similarity	NPC302280
0.7059	Intermediate Similarity	NPC92885
0.7059	Intermediate Similarity	NPC77796
0.7059	Intermediate Similarity	NPC476226
0.7051	Intermediate Similarity	NPC11908
0.7042	Intermediate Similarity	NPC258595
0.7037	Intermediate Similarity	NPC477978
0.7027	Intermediate Similarity	NPC45296
0.7027	Intermediate Similarity	NPC475728
0.7013	Intermediate Similarity	NPC265588
0.7013	Intermediate Similarity	NPC63958
0.7013	Intermediate Similarity	NPC106432
0.7	Intermediate Similarity	NPC476101
0.6974	Remote Similarity	NPC71152
0.6974	Remote Similarity	NPC22134
0.6974	Remote Similarity	NPC100334
0.6974	Remote Similarity	NPC477138
0.6974	Remote Similarity	NPC243342
0.6974	Remote Similarity	NPC91858
0.6974	Remote Similarity	NPC476736
0.6962	Remote Similarity	NPC233295
0.6933	Remote Similarity	NPC301226
0.6933	Remote Similarity	NPC111234
0.6932	Remote Similarity	NPC217329
0.6923	Remote Similarity	NPC84868
0.6923	Remote Similarity	NPC91594
0.6923	Remote Similarity	NPC472746
0.6923	Remote Similarity	NPC471798
0.6923	Remote Similarity	NPC475025
0.6914	Remote Similarity	NPC471408
0.6914	Remote Similarity	NPC296701
0.6914	Remote Similarity	NPC218616
0.6905	Remote Similarity	NPC149224
0.6905	Remote Similarity	NPC476948
0.6905	Remote Similarity	NPC166857
0.6905	Remote Similarity	NPC476932
0.6901	Remote Similarity	NPC101128
0.6901	Remote Similarity	NPC68656
0.6897	Remote Similarity	NPC27531
0.6883	Remote Similarity	NPC3403
0.6883	Remote Similarity	NPC103822
0.6883	Remote Similarity	NPC291503
0.6883	Remote Similarity	NPC34700
0.6883	Remote Similarity	NPC32832
0.6883	Remote Similarity	NPC138374
0.6883	Remote Similarity	NPC185536
0.6883	Remote Similarity	NPC144075
0.6875	Remote Similarity	NPC469802
0.6875	Remote Similarity	NPC206735
0.6875	Remote Similarity	NPC233332
0.6875	Remote Similarity	NPC474978
0.6867	Remote Similarity	NPC137493
0.686	Remote Similarity	NPC76286
0.686	Remote Similarity	NPC295668
0.6857	Remote Similarity	NPC79576
0.6857	Remote Similarity	NPC194208
0.6857	Remote Similarity	NPC282694
0.6849	Remote Similarity	NPC185874
0.6849	Remote Similarity	NPC253303
0.6849	Remote Similarity	NPC139207
0.6849	Remote Similarity	NPC197805
0.6849	Remote Similarity	NPC269077
0.6842	Remote Similarity	NPC211009
0.6842	Remote Similarity	NPC471799
0.6835	Remote Similarity	NPC472501
0.6835	Remote Similarity	NPC472342
0.6835	Remote Similarity	NPC148977
0.6835	Remote Similarity	NPC285761
0.6835	Remote Similarity	NPC301707
0.6829	Remote Similarity	NPC473592
0.6829	Remote Similarity	NPC52108
0.6829	Remote Similarity	NPC474789
0.6829	Remote Similarity	NPC476927
0.6829	Remote Similarity	NPC134481
0.6829	Remote Similarity	NPC82623
0.6824	Remote Similarity	NPC106332
0.6824	Remote Similarity	NPC93411
0.6824	Remote Similarity	NPC473879
0.6824	Remote Similarity	NPC471952
0.6818	Remote Similarity	NPC144202
0.6818	Remote Similarity	NPC201725
0.68	Remote Similarity	NPC145498
0.6795	Remote Similarity	NPC237460
0.6795	Remote Similarity	NPC189883
0.6795	Remote Similarity	NPC265328
0.6795	Remote Similarity	NPC122418
0.6795	Remote Similarity	NPC120098
0.6795	Remote Similarity	NPC134330
0.6795	Remote Similarity	NPC30590
0.6795	Remote Similarity	NPC91573
0.6795	Remote Similarity	NPC290598
0.6795	Remote Similarity	NPC27765
0.6795	Remote Similarity	NPC129165
0.679	Remote Similarity	NPC116202
0.679	Remote Similarity	NPC474683
0.679	Remote Similarity	NPC474759
0.679	Remote Similarity	NPC474752
0.679	Remote Similarity	NPC474731
0.679	Remote Similarity	NPC195334
0.679	Remote Similarity	NPC290495
0.679	Remote Similarity	NPC25554
0.679	Remote Similarity	NPC476646
0.679	Remote Similarity	NPC7505
0.679	Remote Similarity	NPC142163
0.679	Remote Similarity	NPC82986
0.679	Remote Similarity	NPC249423
0.6786	Remote Similarity	NPC286153
0.6786	Remote Similarity	NPC323209
0.6782	Remote Similarity	NPC177641
0.6765	Remote Similarity	NPC135438
0.6757	Remote Similarity	NPC276616
0.6757	Remote Similarity	NPC244790
0.6757	Remote Similarity	NPC32055
0.6757	Remote Similarity	NPC245795
0.6753	Remote Similarity	NPC471797
0.6753	Remote Similarity	NPC62657
0.6753	Remote Similarity	NPC472503
0.6753	Remote Similarity	NPC49168
0.6753	Remote Similarity	NPC5046
0.6753	Remote Similarity	NPC25511
0.6753	Remote Similarity	NPC192638
0.6753	Remote Similarity	NPC308440
0.6753	Remote Similarity	NPC196358
0.6753	Remote Similarity	NPC145552
0.6753	Remote Similarity	NPC254509
0.675	Remote Similarity	NPC291379
0.675	Remote Similarity	NPC47808
0.675	Remote Similarity	NPC80530
0.675	Remote Similarity	NPC263951
0.675	Remote Similarity	NPC129501
0.675	Remote Similarity	NPC305835
0.675	Remote Similarity	NPC273410
0.6747	Remote Similarity	NPC474047
0.6747	Remote Similarity	NPC96055
0.6747	Remote Similarity	NPC306951
0.6744	Remote Similarity	NPC82876
0.6742	Remote Similarity	NPC8774
0.6712	Remote Similarity	NPC475897
0.6712	Remote Similarity	NPC473929
0.6712	Remote Similarity	NPC327815

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 NPC42630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	3010
0.2-0.3	3978
0.3-0.4	1364
0.4-0.5	267
0.5-0.6	224
0.6-0.7	21
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
0.6753	Remote Similarity	NPD4784	Approved
0.6753	Remote Similarity	NPD4785	Approved
0.675	Remote Similarity	NPD7645	Phase 2
0.6711	Remote Similarity	NPD4243	Approved
0.6706	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6456	Remote Similarity	NPD6942	Approved
0.6456	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.629	Remote Similarity	NPD367	Approved
0.625	Remote Similarity	NPD4190	Phase 3
0.625	Remote Similarity	NPD5275	Approved
0.6173	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7638	Approved
0.6162	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4195	Approved
0.6105	Remote Similarity	NPD7639	Approved
0.6105	Remote Similarity	NPD7640	Approved
0.6044	Remote Similarity	NPD5693	Phase 1
0.6026	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6098	Approved
0.593	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6924	Approved
0.5926	Remote Similarity	NPD6926	Approved
0.5914	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7900	Approved
0.5914	Remote Similarity	NPD7748	Approved
0.5909	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5360	Phase 3
0.5875	Remote Similarity	NPD7150	Approved
0.5875	Remote Similarity	NPD7151	Approved
0.5875	Remote Similarity	NPD7152	Approved
0.5873	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.587	Remote Similarity	NPD8035	Phase 2
0.587	Remote Similarity	NPD8034	Phase 2
0.587	Remote Similarity	NPD6079	Approved
0.5862	Remote Similarity	NPD6695	Phase 3
0.5854	Remote Similarity	NPD8264	Approved
0.5851	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7334	Approved
0.5843	Remote Similarity	NPD4623	Approved
0.5843	Remote Similarity	NPD7146	Approved
0.5843	Remote Similarity	NPD3618	Phase 1
0.5843	Remote Similarity	NPD6684	Approved
0.5843	Remote Similarity	NPD5330	Approved
0.5843	Remote Similarity	NPD7521	Approved
0.5843	Remote Similarity	NPD4519	Discontinued
0.5843	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6409	Approved
0.5824	Remote Similarity	NPD6080	Approved
0.5824	Remote Similarity	NPD6673	Approved
0.5824	Remote Similarity	NPD5328	Approved
0.5824	Remote Similarity	NPD6904	Approved
0.5821	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD1145	Discontinued
0.5795	Remote Similarity	NPD4786	Approved
0.5795	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6933	Approved
0.5778	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7144	Approved
0.575	Remote Similarity	NPD4787	Phase 1
0.575	Remote Similarity	NPD7143	Approved
0.5747	Remote Similarity	NPD3667	Approved
0.5747	Remote Similarity	NPD4223	Phase 3
0.5747	Remote Similarity	NPD4221	Approved
0.5745	Remote Similarity	NPD6001	Approved
0.573	Remote Similarity	NPD5329	Approved
0.5729	Remote Similarity	NPD7902	Approved
0.5714	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5737	Approved
0.5714	Remote Similarity	NPD6672	Approved
0.5714	Remote Similarity	NPD6903	Approved
0.5714	Remote Similarity	NPD5208	Approved
0.5714	Remote Similarity	NPD4159	Approved
0.5699	Remote Similarity	NPD7515	Phase 2
0.5698	Remote Similarity	NPD7509	Discontinued
0.5698	Remote Similarity	NPD6931	Approved
0.5698	Remote Similarity	NPD4748	Discontinued
0.5698	Remote Similarity	NPD6930	Phase 2
0.5682	Remote Similarity	NPD4788	Approved
0.567	Remote Similarity	NPD4225	Approved
0.5657	Remote Similarity	NPD7632	Discontinued
0.5647	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4202	Approved
0.5638	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD6922	Approved
0.5625	Remote Similarity	NPD6923	Approved
0.5618	Remote Similarity	NPD3668	Phase 3
0.5618	Remote Similarity	NPD4197	Approved
0.5604	Remote Similarity	NPD7524	Approved
0.5604	Remote Similarity	NPD7750	Discontinued

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