NPASS Compound

Structure

NPC283247 OpenBabel07101718292D 21 22 0 0 1 0 0 0 0 0999 V2000 -7.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8660 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 0.3660 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 -6.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8660 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3660 0.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -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 0 0 0 0 0 0 0 0 0 0 -5.8660 -0.5000 0.0000 C 0 0 2 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 8 2 0 0 0 0 2 14 2 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 16 15 1 1 0 0 0 17 20 1 1 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.529
LogD:	4.686
LogS:	-5.663
# Rotatable Bonds:	5
TPSA:	12.53
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	4.589
Fsp3:	0.7
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:	-4.678
MDCK Permeability:	2.116511677741073e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.577
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	95.46046447753906%
Volume Distribution (VD):	1.986
Pgp-substrate:	3.4356985092163086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.592
CYP2C19-inhibitor:	0.248
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.552
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	3.613
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.727
Carcinogencity:	0.082
Eye Corrosion:	0.936
Eye Irritation:	0.871
Respiratory Toxicity:	0.445

Download Data

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

Natural Product: NPC283247

Natural Product ID:	NPC283247
*Common Name:**	(R)-2,2-Dimethyl-3-(3-((1S,3R,4R)-4-Methyl-3-(Prop-1-En-2-Yl)-4-Vinylcyclohexyl)But-2-Enyl)Oxirane
IUPAC Name:	(3R)-3-[(E)-3-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]but-2-enyl]-2,2-dimethyloxirane
Synonyms:
Standard InCHIKey:	PLMPUHCOGGTVIR-JZXJGBJOSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-8-20(7)12-11-16(13-17(20)14(2)3)15(4)9-10-18-19(5,6)21-18/h8-9,16-18H,1-2,10-13H2,3-7H3/b15-9+/t16-,17+,18+,20-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)/C(=C/C[C@H]1OC1(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476287
PubChem CID:	42608262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002872] Elemane sesquiterpenoids

*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
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	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
Others	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	5.0	mm	PMID[464270]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	0.0	mm	PMID[464270]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.64	ug.mL-1	PMID[464270]

☑ 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 NPC283247 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	213
0.1-0.2	2477
0.2-0.3	14845
0.3-0.4	12112
0.4-0.5	7980
0.5-0.6	4493
0.6-0.7	553
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8308	Intermediate Similarity	NPC250977
0.8136	Intermediate Similarity	NPC165755
0.8	Intermediate Similarity	NPC104644
0.7869	Intermediate Similarity	NPC223604
0.7727	Intermediate Similarity	NPC287744
0.7727	Intermediate Similarity	NPC140233
0.7586	Intermediate Similarity	NPC124851
0.7538	Intermediate Similarity	NPC176621
0.7536	Intermediate Similarity	NPC208999
0.7467	Intermediate Similarity	NPC233295
0.7463	Intermediate Similarity	NPC290367
0.7391	Intermediate Similarity	NPC114651
0.7368	Intermediate Similarity	NPC233332
0.7368	Intermediate Similarity	NPC474592
0.7361	Intermediate Similarity	NPC471799
0.7344	Intermediate Similarity	NPC11130
0.7324	Intermediate Similarity	NPC145498
0.7297	Intermediate Similarity	NPC265588
0.7286	Intermediate Similarity	NPC476945
0.726	Intermediate Similarity	NPC471797
0.7246	Intermediate Similarity	NPC279434
0.7246	Intermediate Similarity	NPC222366
0.7246	Intermediate Similarity	NPC286669
0.7246	Intermediate Similarity	NPC476039
0.7222	Intermediate Similarity	NPC167706
0.7222	Intermediate Similarity	NPC242001
0.7206	Intermediate Similarity	NPC225415
0.7206	Intermediate Similarity	NPC329698
0.72	Intermediate Similarity	NPC470750
0.72	Intermediate Similarity	NPC470751
0.7167	Intermediate Similarity	NPC17518
0.7167	Intermediate Similarity	NPC22765
0.7164	Intermediate Similarity	NPC294304
0.7164	Intermediate Similarity	NPC469728
0.7164	Intermediate Similarity	NPC228574
0.7143	Intermediate Similarity	NPC197805
0.7143	Intermediate Similarity	NPC474477
0.7125	Intermediate Similarity	NPC474189
0.7125	Intermediate Similarity	NPC474349
0.7123	Intermediate Similarity	NPC182717
0.7105	Intermediate Similarity	NPC476314
0.7101	Intermediate Similarity	NPC163678
0.7089	Intermediate Similarity	NPC475789
0.7089	Intermediate Similarity	NPC23748
0.7089	Intermediate Similarity	NPC49208
0.7083	Intermediate Similarity	NPC189745
0.7083	Intermediate Similarity	NPC49422
0.7083	Intermediate Similarity	NPC34834
0.7083	Intermediate Similarity	NPC9161
0.7067	Intermediate Similarity	NPC113733
0.7051	Intermediate Similarity	NPC116202
0.7027	Intermediate Similarity	NPC243342
0.7027	Intermediate Similarity	NPC477138
0.7015	Intermediate Similarity	NPC127824
0.7013	Intermediate Similarity	NPC153987
0.7013	Intermediate Similarity	NPC44083
0.7013	Intermediate Similarity	NPC100906
0.7	Intermediate Similarity	NPC306951
0.7	Intermediate Similarity	NPC474047
0.7	Intermediate Similarity	NPC149680
0.7	Intermediate Similarity	NPC327815
0.6986	Remote Similarity	NPC110799
0.6974	Remote Similarity	NPC34019
0.6974	Remote Similarity	NPC283619
0.6974	Remote Similarity	NPC91594
0.6974	Remote Similarity	NPC471798
0.6974	Remote Similarity	NPC155986
0.6974	Remote Similarity	NPC198968
0.6974	Remote Similarity	NPC318495
0.697	Remote Similarity	NPC60772
0.6944	Remote Similarity	NPC167272
0.6944	Remote Similarity	NPC304690
0.6944	Remote Similarity	NPC476431
0.6944	Remote Similarity	NPC74722
0.6944	Remote Similarity	NPC269877
0.6933	Remote Similarity	NPC285893
0.6933	Remote Similarity	NPC291503
0.6933	Remote Similarity	NPC230301
0.6933	Remote Similarity	NPC136188
0.6933	Remote Similarity	NPC162742
0.6933	Remote Similarity	NPC22105
0.6933	Remote Similarity	NPC304309
0.6933	Remote Similarity	NPC12696
0.6933	Remote Similarity	NPC134847
0.6933	Remote Similarity	NPC288035
0.6933	Remote Similarity	NPC28657
0.6923	Remote Similarity	NPC209944
0.6923	Remote Similarity	NPC164840
0.6923	Remote Similarity	NPC241290
0.6923	Remote Similarity	NPC210316
0.6923	Remote Similarity	NPC39068
0.6912	Remote Similarity	NPC60565
0.6912	Remote Similarity	NPC475251
0.6892	Remote Similarity	NPC329763
0.6892	Remote Similarity	NPC68443
0.6892	Remote Similarity	NPC474140
0.6883	Remote Similarity	NPC83351
0.6883	Remote Similarity	NPC167891
0.6883	Remote Similarity	NPC18603
0.6883	Remote Similarity	NPC307965
0.6883	Remote Similarity	NPC76931
0.6866	Remote Similarity	NPC83838
0.6866	Remote Similarity	NPC143810
0.6849	Remote Similarity	NPC475728
0.6849	Remote Similarity	NPC92801
0.6842	Remote Similarity	NPC470362
0.6842	Remote Similarity	NPC321381
0.6842	Remote Similarity	NPC321016
0.6842	Remote Similarity	NPC240604
0.6842	Remote Similarity	NPC106364
0.6842	Remote Similarity	NPC300324
0.6842	Remote Similarity	NPC476607
0.6842	Remote Similarity	NPC107059
0.6842	Remote Similarity	NPC129165
0.6842	Remote Similarity	NPC134330
0.6835	Remote Similarity	NPC264245
0.6835	Remote Similarity	NPC25554
0.6835	Remote Similarity	NPC47761
0.6835	Remote Similarity	NPC142163
0.6835	Remote Similarity	NPC108476
0.6829	Remote Similarity	NPC125399
0.6818	Remote Similarity	NPC65786
0.6818	Remote Similarity	NPC101285
0.6818	Remote Similarity	NPC7491
0.6818	Remote Similarity	NPC27853
0.6818	Remote Similarity	NPC13789
0.6806	Remote Similarity	NPC139785
0.6806	Remote Similarity	NPC216460
0.6806	Remote Similarity	NPC94192
0.6806	Remote Similarity	NPC305698
0.6806	Remote Similarity	NPC32055
0.6806	Remote Similarity	NPC160209
0.68	Remote Similarity	NPC71152
0.68	Remote Similarity	NPC201048
0.68	Remote Similarity	NPC329090
0.68	Remote Similarity	NPC476366
0.68	Remote Similarity	NPC27395
0.68	Remote Similarity	NPC100334
0.68	Remote Similarity	NPC91858
0.6795	Remote Similarity	NPC328714
0.6795	Remote Similarity	NPC476177
0.6795	Remote Similarity	NPC291379
0.6795	Remote Similarity	NPC283789
0.6795	Remote Similarity	NPC242767
0.6765	Remote Similarity	NPC471081
0.6761	Remote Similarity	NPC202017
0.6761	Remote Similarity	NPC476406
0.6757	Remote Similarity	NPC164022
0.6753	Remote Similarity	NPC470758
0.6753	Remote Similarity	NPC470711
0.6753	Remote Similarity	NPC325946
0.675	Remote Similarity	NPC471218
0.675	Remote Similarity	NPC49964
0.675	Remote Similarity	NPC5985
0.675	Remote Similarity	NPC155521
0.6724	Remote Similarity	NPC190232
0.6724	Remote Similarity	NPC105246
0.6716	Remote Similarity	NPC181872
0.6714	Remote Similarity	NPC469662
0.6712	Remote Similarity	NPC474248
0.6712	Remote Similarity	NPC9942
0.6712	Remote Similarity	NPC471560
0.6712	Remote Similarity	NPC329656
0.6711	Remote Similarity	NPC66566
0.6711	Remote Similarity	NPC319090
0.6711	Remote Similarity	NPC69383
0.6711	Remote Similarity	NPC477923
0.6711	Remote Similarity	NPC113639
0.6711	Remote Similarity	NPC32832
0.6711	Remote Similarity	NPC471468
0.6711	Remote Similarity	NPC141071
0.6711	Remote Similarity	NPC328104
0.6711	Remote Similarity	NPC313179
0.6711	Remote Similarity	NPC257347
0.6711	Remote Similarity	NPC471723
0.6711	Remote Similarity	NPC171148
0.6709	Remote Similarity	NPC234193
0.6709	Remote Similarity	NPC269791
0.6707	Remote Similarity	NPC274448
0.6707	Remote Similarity	NPC157257
0.6667	Remote Similarity	NPC474989
0.6667	Remote Similarity	NPC132386
0.6667	Remote Similarity	NPC312328
0.6667	Remote Similarity	NPC93411
0.6667	Remote Similarity	NPC22955
0.6667	Remote Similarity	NPC45782
0.6667	Remote Similarity	NPC69649
0.6667	Remote Similarity	NPC144947
0.6667	Remote Similarity	NPC474005
0.6667	Remote Similarity	NPC296337
0.6667	Remote Similarity	NPC473943
0.6667	Remote Similarity	NPC139206
0.6667	Remote Similarity	NPC285761
0.6667	Remote Similarity	NPC107783
0.6667	Remote Similarity	NPC86683
0.6667	Remote Similarity	NPC470396
0.6667	Remote Similarity	NPC99168
0.6667	Remote Similarity	NPC41160
0.6667	Remote Similarity	NPC65897
0.6667	Remote Similarity	NPC302041

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 NPC283247 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2622
0.2-0.3	4304
0.3-0.4	1515
0.4-0.5	327
0.5-0.6	148
0.6-0.7	24
0.7-0.8	0
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
0.7083	Intermediate Similarity	NPD7143	Approved
0.7083	Intermediate Similarity	NPD7144	Approved
0.6986	Remote Similarity	NPD7150	Approved
0.6986	Remote Similarity	NPD7151	Approved
0.6986	Remote Similarity	NPD7152	Approved
0.6944	Remote Similarity	NPD6923	Approved
0.6944	Remote Similarity	NPD6922	Approved
0.6933	Remote Similarity	NPD6942	Approved
0.6933	Remote Similarity	NPD7339	Approved
0.68	Remote Similarity	NPD6926	Approved
0.68	Remote Similarity	NPD4784	Approved
0.68	Remote Similarity	NPD6924	Approved
0.68	Remote Similarity	NPD4785	Approved
0.6753	Remote Similarity	NPD6932	Approved
0.6724	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6933	Approved
0.6582	Remote Similarity	NPD7645	Phase 2
0.6533	Remote Similarity	NPD4243	Approved
0.65	Remote Similarity	NPD7514	Phase 3
0.65	Remote Similarity	NPD7332	Phase 2
0.65	Remote Similarity	NPD7525	Registered
0.6479	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6695	Phase 3
0.6456	Remote Similarity	NPD7145	Approved
0.642	Remote Similarity	NPD6902	Approved
0.6418	Remote Similarity	NPD4219	Approved
0.6389	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6683	Phase 2
0.6349	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6925	Approved
0.6329	Remote Similarity	NPD5776	Phase 2
0.6296	Remote Similarity	NPD6931	Approved
0.6296	Remote Similarity	NPD6930	Phase 2
0.6296	Remote Similarity	NPD7509	Discontinued
0.6235	Remote Similarity	NPD6684	Approved
0.6235	Remote Similarity	NPD7521	Approved
0.6235	Remote Similarity	NPD7334	Approved
0.6235	Remote Similarity	NPD7146	Approved
0.6235	Remote Similarity	NPD6409	Approved
0.6235	Remote Similarity	NPD5330	Approved
0.622	Remote Similarity	NPD6898	Phase 1
0.6207	Remote Similarity	NPD6051	Approved
0.6197	Remote Similarity	NPD368	Approved
0.619	Remote Similarity	NPD4786	Approved
0.6173	Remote Similarity	NPD6929	Approved
0.6163	Remote Similarity	NPD7750	Discontinued
0.6163	Remote Similarity	NPD7524	Approved
0.6145	Remote Similarity	NPD3667	Approved
0.6133	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD8262	Approved
0.6092	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6903	Approved
0.6076	Remote Similarity	NPD5275	Approved
0.6076	Remote Similarity	NPD4190	Phase 3
0.6053	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD287	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5977	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4195	Approved
0.5974	Remote Similarity	NPD4691	Approved
0.5974	Remote Similarity	NPD4747	Approved
0.5949	Remote Similarity	NPD4058	Approved
0.5949	Remote Similarity	NPD5733	Approved
0.5949	Remote Similarity	NPD4687	Approved
0.593	Remote Similarity	NPD6893	Approved
0.5909	Remote Similarity	NPD6672	Approved
0.5909	Remote Similarity	NPD5737	Approved
0.5904	Remote Similarity	NPD4748	Discontinued
0.5889	Remote Similarity	NPD7637	Suspended
0.5889	Remote Similarity	NPD7087	Discontinued
0.5875	Remote Similarity	NPD8039	Approved
0.5862	Remote Similarity	NPD6098	Approved
0.5833	Remote Similarity	NPD1145	Discontinued
0.5823	Remote Similarity	NPD4732	Discontinued
0.5814	Remote Similarity	NPD3666	Approved
0.5814	Remote Similarity	NPD3133	Approved
0.5814	Remote Similarity	NPD3665	Phase 1
0.5795	Remote Similarity	NPD3573	Approved
0.5778	Remote Similarity	NPD3168	Discontinued
0.5765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7748	Approved
0.5761	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6079	Approved
0.5699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD5276	Approved
0.5682	Remote Similarity	NPD3618	Phase 1
0.5667	Remote Similarity	NPD6080	Approved
0.5667	Remote Similarity	NPD6673	Approved
0.5667	Remote Similarity	NPD6904	Approved
0.5667	Remote Similarity	NPD5328	Approved
0.5657	Remote Similarity	NPD6008	Approved
0.5632	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6648	Approved
0.5604	Remote Similarity	NPD7136	Phase 2
0.5604	Remote Similarity	NPD5207	Approved

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