NPASS Compound

Structure

CID11130 OpenBabel06191715342D 21 21 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 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 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 18 3 1 6 0 0 0 18 19 1 0 0 0 0 19 12 1 6 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.29
Volume:	352.073
LogP:	6.847
LogD:	5.341
LogS:	-5.909
# Rotatable Bonds:	8
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	3.836
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.461
MDCK Permeability:	1.1126390745630488e-05
Pgp-inhibitor:	0.482
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.577
Plasma Protein Binding (PPB):	97.52130889892578%
Volume Distribution (VD):	2.577
Pgp-substrate:	2.1249115467071533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.28
CYP1A2-substrate:	0.491
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.266
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.333
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	6.485
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.97
Carcinogencity:	0.04
Eye Corrosion:	0.946
Eye Irritation:	0.922
Respiratory Toxicity:	0.449

Download Data

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

Natural Product: NPC11130

Natural Product ID:	NPC11130
*Common Name:**	Cassipourol
IUPAC Name:	(E)-3,7-dimethyl-9-[(1S,6S)-2,2,6-trimethylcyclohexyl]non-2-en-1-ol
Synonyms:	Cassipourol
Standard InCHIKey:	UDNYCQANCWSNDB-MBNCDAFSSA-N
Standard InCHI:	InChI=1S/C20H38O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h13,16,18-19,21H,6-12,14-15H2,1-5H3/b17-13+/t16?,18-,19-/m0/s1
SMILES:	OC/C=C(/CCCC(CC[C@H]1[C@@H](C)CCCC1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482226
PubChem CID:	11500301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001606] Retinoids

*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
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[16499334]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[18181575]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	2.4	ug.mL-1	PMID[520734]

☑ 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 NPC11130 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	125
0.1-0.2	2423
0.2-0.3	15143
0.3-0.4	12542
0.4-0.5	7585
0.5-0.6	3795
0.6-0.7	947
0.7-0.8	119
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC309825
0.8679	High Similarity	NPC26960
0.8679	High Similarity	NPC182102
0.8548	High Similarity	NPC68703
0.8548	High Similarity	NPC69649
0.8475	Intermediate Similarity	NPC176621
0.8421	Intermediate Similarity	NPC249645
0.8421	Intermediate Similarity	NPC55412
0.8254	Intermediate Similarity	NPC114651
0.8167	Intermediate Similarity	NPC234264
0.8167	Intermediate Similarity	NPC47840
0.8154	Intermediate Similarity	NPC189745
0.8154	Intermediate Similarity	NPC34834
0.8033	Intermediate Similarity	NPC469728
0.7969	Intermediate Similarity	NPC171225
0.7937	Intermediate Similarity	NPC107258
0.791	Intermediate Similarity	NPC474743
0.7903	Intermediate Similarity	NPC124112
0.7869	Intermediate Similarity	NPC471081
0.7857	Intermediate Similarity	NPC244038
0.7812	Intermediate Similarity	NPC149680
0.7812	Intermediate Similarity	NPC250977
0.7812	Intermediate Similarity	NPC259156
0.7812	Intermediate Similarity	NPC286669
0.7812	Intermediate Similarity	NPC222366
0.7812	Intermediate Similarity	NPC242945
0.7812	Intermediate Similarity	NPC476039
0.7794	Intermediate Similarity	NPC306727
0.7794	Intermediate Similarity	NPC201048
0.7794	Intermediate Similarity	NPC476366
0.7778	Intermediate Similarity	NPC225415
0.7778	Intermediate Similarity	NPC290367
0.7778	Intermediate Similarity	NPC107540
0.7778	Intermediate Similarity	NPC475704
0.7778	Intermediate Similarity	NPC329698
0.7727	Intermediate Similarity	NPC474248
0.7692	Intermediate Similarity	NPC197805
0.7681	Intermediate Similarity	NPC32832
0.7656	Intermediate Similarity	NPC163678
0.7656	Intermediate Similarity	NPC19569
0.7636	Intermediate Similarity	NPC124851
0.7627	Intermediate Similarity	NPC298299
0.7576	Intermediate Similarity	NPC471238
0.7576	Intermediate Similarity	NPC160209
0.7576	Intermediate Similarity	NPC216460
0.7576	Intermediate Similarity	NPC96484
0.7576	Intermediate Similarity	NPC208999
0.7571	Intermediate Similarity	NPC470749
0.7571	Intermediate Similarity	NPC244488
0.7571	Intermediate Similarity	NPC247325
0.7541	Intermediate Similarity	NPC181872
0.7538	Intermediate Similarity	NPC202017
0.7538	Intermediate Similarity	NPC476406
0.7538	Intermediate Similarity	NPC135650
0.7538	Intermediate Similarity	NPC279434
0.75	Intermediate Similarity	NPC474643
0.75	Intermediate Similarity	NPC477792
0.75	Intermediate Similarity	NPC309300
0.75	Intermediate Similarity	NPC22765
0.75	Intermediate Similarity	NPC96793
0.75	Intermediate Similarity	NPC17518
0.75	Intermediate Similarity	NPC48891
0.75	Intermediate Similarity	NPC473865
0.75	Intermediate Similarity	NPC323424
0.7465	Intermediate Similarity	NPC470711
0.7465	Intermediate Similarity	NPC91594
0.7465	Intermediate Similarity	NPC470758
0.7463	Intermediate Similarity	NPC473893
0.7463	Intermediate Similarity	NPC471560
0.7429	Intermediate Similarity	NPC313179
0.7429	Intermediate Similarity	NPC69383
0.7429	Intermediate Similarity	NPC171148
0.7419	Intermediate Similarity	NPC475931
0.7419	Intermediate Similarity	NPC122239
0.7361	Intermediate Similarity	NPC297996
0.7361	Intermediate Similarity	NPC239098
0.7361	Intermediate Similarity	NPC167891
0.7361	Intermediate Similarity	NPC476314
0.7361	Intermediate Similarity	NPC83351
0.7353	Intermediate Similarity	NPC145498
0.7344	Intermediate Similarity	NPC474155
0.7344	Intermediate Similarity	NPC81615
0.7344	Intermediate Similarity	NPC473759
0.7344	Intermediate Similarity	NPC283247
0.7333	Intermediate Similarity	NPC474644
0.7333	Intermediate Similarity	NPC329686
0.7324	Intermediate Similarity	NPC265588
0.7324	Intermediate Similarity	NPC253190
0.7313	Intermediate Similarity	NPC32055
0.7313	Intermediate Similarity	NPC476945
0.7302	Intermediate Similarity	NPC240506
0.7286	Intermediate Similarity	NPC469533
0.7286	Intermediate Similarity	NPC469534
0.7286	Intermediate Similarity	NPC469593
0.7273	Intermediate Similarity	NPC185587
0.7273	Intermediate Similarity	NPC86683
0.726	Intermediate Similarity	NPC28862
0.726	Intermediate Similarity	NPC109546
0.726	Intermediate Similarity	NPC84694
0.726	Intermediate Similarity	NPC209430
0.726	Intermediate Similarity	NPC242767
0.726	Intermediate Similarity	NPC81306
0.726	Intermediate Similarity	NPC30986
0.726	Intermediate Similarity	NPC143182
0.726	Intermediate Similarity	NPC47982
0.7246	Intermediate Similarity	NPC471272
0.7246	Intermediate Similarity	NPC471271
0.7246	Intermediate Similarity	NPC471268
0.7246	Intermediate Similarity	NPC167706
0.7246	Intermediate Similarity	NPC242001
0.7206	Intermediate Similarity	NPC9942
0.7206	Intermediate Similarity	NPC269877
0.7206	Intermediate Similarity	NPC167272
0.7188	Intermediate Similarity	NPC41160
0.7188	Intermediate Similarity	NPC210346
0.7188	Intermediate Similarity	NPC475251
0.717	Intermediate Similarity	NPC269823
0.7162	Intermediate Similarity	NPC306095
0.7162	Intermediate Similarity	NPC281880
0.7162	Intermediate Similarity	NPC234193
0.7162	Intermediate Similarity	NPC96362
0.7162	Intermediate Similarity	NPC295131
0.7143	Intermediate Similarity	NPC471799
0.7143	Intermediate Similarity	NPC130665
0.7143	Intermediate Similarity	NPC474140
0.7143	Intermediate Similarity	NPC182717
0.7143	Intermediate Similarity	NPC68443
0.7123	Intermediate Similarity	NPC474216
0.7123	Intermediate Similarity	NPC11908
0.7121	Intermediate Similarity	NPC187619
0.7101	Intermediate Similarity	NPC49422
0.7101	Intermediate Similarity	NPC9161
0.7083	Intermediate Similarity	NPC19907
0.7077	Intermediate Similarity	NPC174956
0.7067	Intermediate Similarity	NPC209620
0.7067	Intermediate Similarity	NPC4166
0.7067	Intermediate Similarity	NPC159148
0.7067	Intermediate Similarity	NPC249423
0.7067	Intermediate Similarity	NPC23852
0.7067	Intermediate Similarity	NPC476646
0.7067	Intermediate Similarity	NPC264245
0.7059	Intermediate Similarity	NPC117804
0.7049	Intermediate Similarity	NPC251666
0.7049	Intermediate Similarity	NPC148163
0.7049	Intermediate Similarity	NPC148216
0.7049	Intermediate Similarity	NPC130209
0.7049	Intermediate Similarity	NPC232247
0.7042	Intermediate Similarity	NPC91858
0.7042	Intermediate Similarity	NPC477138
0.7042	Intermediate Similarity	NPC243342
0.7042	Intermediate Similarity	NPC471797
0.7042	Intermediate Similarity	NPC78527
0.7042	Intermediate Similarity	NPC100334
0.7037	Intermediate Similarity	NPC256766
0.7037	Intermediate Similarity	NPC213538
0.7031	Intermediate Similarity	NPC66020
0.7015	Intermediate Similarity	NPC162309
0.7	Intermediate Similarity	NPC471662
0.7	Intermediate Similarity	NPC95863
0.7	Intermediate Similarity	NPC110799
0.7	Intermediate Similarity	NPC133253
0.7	Intermediate Similarity	NPC23954
0.6986	Remote Similarity	NPC74995
0.6984	Remote Similarity	NPC226848
0.6984	Remote Similarity	NPC60772
0.6984	Remote Similarity	NPC155025
0.6974	Remote Similarity	NPC311092
0.6974	Remote Similarity	NPC202389
0.6974	Remote Similarity	NPC155521
0.6974	Remote Similarity	NPC296701
0.6974	Remote Similarity	NPC218616
0.6974	Remote Similarity	NPC2524
0.6974	Remote Similarity	NPC101462
0.6974	Remote Similarity	NPC49964
0.6974	Remote Similarity	NPC189972
0.6974	Remote Similarity	NPC50964
0.6974	Remote Similarity	NPC87489
0.697	Remote Similarity	NPC52449
0.697	Remote Similarity	NPC169275
0.697	Remote Similarity	NPC68656
0.6949	Remote Similarity	NPC474495
0.6949	Remote Similarity	NPC473672
0.6944	Remote Similarity	NPC304309
0.6944	Remote Similarity	NPC477923
0.6944	Remote Similarity	NPC471723
0.6944	Remote Similarity	NPC288035
0.6944	Remote Similarity	NPC136188
0.6944	Remote Similarity	NPC134847
0.6944	Remote Similarity	NPC133580
0.6944	Remote Similarity	NPC22105
0.6944	Remote Similarity	NPC291503
0.6944	Remote Similarity	NPC66566
0.6944	Remote Similarity	NPC257347
0.6944	Remote Similarity	NPC162742
0.6944	Remote Similarity	NPC285893
0.6944	Remote Similarity	NPC28657
0.6944	Remote Similarity	NPC471468
0.6944	Remote Similarity	NPC141071
0.6944	Remote Similarity	NPC230301
0.6933	Remote Similarity	NPC209944

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 NPC11130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	2695
0.2-0.3	4288
0.3-0.4	1531
0.4-0.5	342
0.5-0.6	123
0.6-0.7	40
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD4219	Approved
0.7429	Intermediate Similarity	NPD8264	Approved
0.7206	Intermediate Similarity	NPD6922	Approved
0.7206	Intermediate Similarity	NPD6923	Approved
0.7123	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7143	Approved
0.7101	Intermediate Similarity	NPD7144	Approved
0.7049	Intermediate Similarity	NPD342	Phase 1
0.7	Intermediate Similarity	NPD7150	Approved
0.7	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD7151	Approved
0.6986	Remote Similarity	NPD5776	Phase 2
0.6986	Remote Similarity	NPD6925	Approved
0.6944	Remote Similarity	NPD6942	Approved
0.6944	Remote Similarity	NPD7339	Approved
0.6933	Remote Similarity	NPD7332	Phase 2
0.6933	Remote Similarity	NPD7514	Phase 3
0.6923	Remote Similarity	NPD4191	Approved
0.6923	Remote Similarity	NPD368	Approved
0.6923	Remote Similarity	NPD4192	Approved
0.6923	Remote Similarity	NPD4193	Approved
0.6923	Remote Similarity	NPD4194	Approved
0.6892	Remote Similarity	NPD7145	Approved
0.6842	Remote Similarity	NPD6902	Approved
0.6806	Remote Similarity	NPD6926	Approved
0.6806	Remote Similarity	NPD6924	Approved
0.68	Remote Similarity	NPD6929	Approved
0.6727	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6930	Phase 2
0.6711	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD4265	Approved
0.6623	Remote Similarity	NPD6898	Phase 1
0.6622	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6933	Approved
0.6579	Remote Similarity	NPD7645	Phase 2
0.6533	Remote Similarity	NPD6932	Approved
0.6528	Remote Similarity	NPD4243	Approved
0.6494	Remote Similarity	NPD7525	Registered
0.6456	Remote Similarity	NPD6695	Phase 3
0.6375	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6683	Phase 2
0.6351	Remote Similarity	NPD4784	Approved
0.6351	Remote Similarity	NPD4785	Approved
0.6341	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8262	Approved
0.6296	Remote Similarity	NPD6893	Approved
0.6282	Remote Similarity	NPD7509	Discontinued
0.6234	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4732	Discontinued
0.6173	Remote Similarity	NPD4786	Approved
0.6145	Remote Similarity	NPD7750	Discontinued
0.6145	Remote Similarity	NPD7524	Approved
0.6125	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4190	Phase 3
0.6053	Remote Similarity	NPD5275	Approved
0.6047	Remote Similarity	NPD7637	Suspended
0.6027	Remote Similarity	NPD4137	Phase 3
0.5976	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3665	Phase 1
0.5976	Remote Similarity	NPD3666	Approved
0.5976	Remote Similarity	NPD3133	Approved
0.597	Remote Similarity	NPD287	Approved
0.5946	Remote Similarity	NPD4691	Approved
0.5946	Remote Similarity	NPD4747	Approved
0.5946	Remote Similarity	NPD6939	Phase 2
0.5946	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.593	Remote Similarity	NPD7136	Phase 2
0.5926	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD5733	Approved
0.5867	Remote Similarity	NPD5276	Approved
0.5862	Remote Similarity	NPD7087	Discontinued
0.5844	Remote Similarity	NPD8039	Approved
0.5833	Remote Similarity	NPD4519	Discontinued
0.5833	Remote Similarity	NPD3618	Phase 1
0.5833	Remote Similarity	NPD5279	Phase 3
0.5833	Remote Similarity	NPD4623	Approved
0.5818	Remote Similarity	NPD319	Phase 1
0.5814	Remote Similarity	NPD5328	Approved
0.5761	Remote Similarity	NPD7640	Approved
0.5761	Remote Similarity	NPD7639	Approved
0.575	Remote Similarity	NPD4195	Approved
0.5714	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4058	Approved
0.5714	Remote Similarity	NPD4687	Approved
0.5714	Remote Similarity	NPD1696	Phase 3
0.5682	Remote Similarity	NPD6079	Approved
0.5682	Remote Similarity	NPD7515	Phase 2
0.5679	Remote Similarity	NPD4695	Discontinued
0.5679	Remote Similarity	NPD4821	Approved
0.5679	Remote Similarity	NPD4820	Approved
0.5679	Remote Similarity	NPD4822	Approved
0.5679	Remote Similarity	NPD4748	Discontinued
0.5679	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD4819	Approved
0.5663	Remote Similarity	NPD5331	Approved
0.5663	Remote Similarity	NPD5332	Approved
0.5663	Remote Similarity	NPD5362	Discontinued
0.5652	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD4225	Approved
0.5632	Remote Similarity	NPD6051	Approved
0.5632	Remote Similarity	NPD4753	Phase 2
0.5625	Remote Similarity	NPD4271	Approved
0.5625	Remote Similarity	NPD4268	Approved
0.561	Remote Similarity	NPD4790	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