NPASS Compound

Structure

CID163678 OpenBabel06191715532D 21 23 0 0 1 0 0 0 0 0999 V2000 -4.2711 1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4676 2.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5640 1.2412 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 -0.0000 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 -1.7321 -0.0000 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 0.0000 -1.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 18 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	4.279
LogD:	3.654
LogS:	-4.822
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.488
Fsp3:	0.8
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:	-4.754
MDCK Permeability:	1.096889900509268e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355
Plasma Protein Binding (PPB):	97.99394226074219%
Volume Distribution (VD):	1.75
Pgp-substrate:	1.9283010959625244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.465
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.194
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.211
CYP2D6-substrate:	0.684
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.501

ADMET: Excretion

Clearance (CL):	4.316
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.812
Carcinogencity:	0.087
Eye Corrosion:	0.429
Eye Irritation:	0.839
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC163678

Natural Product ID:	NPC163678
*Common Name:**	[(1R,4Ar,7R,10As)-7-Ethenyl-1,4A,7-Trimethyl-3,4,5,6,8,9,10,10A-Octahydro-2H-Phenanthren-1-Yl]Methanol
IUPAC Name:	[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-1-yl]methanol
Synonyms:
Standard InCHIKey:	KVGUVNVWQKGXAA-ZRNYENFQSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-5-18(2)12-9-16-15(13-18)7-8-17-19(3,14-21)10-6-11-20(16,17)4/h5,17,21H,1,6-14H2,2-4H3/t17-,18-,19+,20+/m1/s1
SMILES:	C=C[C@]1(C)CCC2=C(C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491704
PubChem CID:	44566217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33152	calceolaria pinifolia	Species	Calceolariaceae	Eukaryota	aerial part	46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (3021 S; 6940 W)	1997-Jan	PMID[12608857]
NPO1761	Ursinia sericea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7881	Parmelia verrucigera	Species	Parmeliaceae	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	32.0	ug.mL-1	PMID[497061]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[497061]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[497061]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[497061]

☑ 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 NPC163678 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	157
0.1-0.2	1672
0.2-0.3	11706
0.3-0.4	14629
0.4-0.5	7573
0.5-0.6	4813
0.6-0.7	1761
0.7-0.8	340
0.8-0.85	35
0.85-0.9	5
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9516	High Similarity	NPC222366
0.9516	High Similarity	NPC476039
0.9516	High Similarity	NPC286669
0.9365	High Similarity	NPC197805
0.9219	High Similarity	NPC216460
0.9219	High Similarity	NPC32055
0.9091	High Similarity	NPC110799
0.8696	High Similarity	NPC471468
0.8676	High Similarity	NPC471799
0.8676	High Similarity	NPC182717
0.8657	High Similarity	NPC145498
0.8636	High Similarity	NPC208999
0.8615	High Similarity	NPC149680
0.8571	High Similarity	NPC470362
0.8551	High Similarity	NPC471797
0.8529	High Similarity	NPC242001
0.8382	Intermediate Similarity	NPC34834
0.8358	Intermediate Similarity	NPC160209
0.8333	Intermediate Similarity	NPC279434
0.831	Intermediate Similarity	NPC134330
0.831	Intermediate Similarity	NPC202642
0.831	Intermediate Similarity	NPC106432
0.831	Intermediate Similarity	NPC46160
0.831	Intermediate Similarity	NPC113733
0.831	Intermediate Similarity	NPC129165
0.8308	Intermediate Similarity	NPC290367
0.8286	Intermediate Similarity	NPC91858
0.8286	Intermediate Similarity	NPC477138
0.8286	Intermediate Similarity	NPC243342
0.8286	Intermediate Similarity	NPC100334
0.8235	Intermediate Similarity	NPC471560
0.8209	Intermediate Similarity	NPC171225
0.8209	Intermediate Similarity	NPC68703
0.8209	Intermediate Similarity	NPC69649
0.8209	Intermediate Similarity	NPC114651
0.8194	Intermediate Similarity	NPC471798
0.8194	Intermediate Similarity	NPC214570
0.8194	Intermediate Similarity	NPC91594
0.8169	Intermediate Similarity	NPC134847
0.8169	Intermediate Similarity	NPC22105
0.8169	Intermediate Similarity	NPC121744
0.8169	Intermediate Similarity	NPC322353
0.8169	Intermediate Similarity	NPC285893
0.8169	Intermediate Similarity	NPC304309
0.8169	Intermediate Similarity	NPC138374
0.8169	Intermediate Similarity	NPC471723
0.8169	Intermediate Similarity	NPC257347
0.8169	Intermediate Similarity	NPC291503
0.8169	Intermediate Similarity	NPC230301
0.8169	Intermediate Similarity	NPC141071
0.8169	Intermediate Similarity	NPC28657
0.8169	Intermediate Similarity	NPC162742
0.8169	Intermediate Similarity	NPC34700
0.8169	Intermediate Similarity	NPC288035
0.8169	Intermediate Similarity	NPC118508
0.8169	Intermediate Similarity	NPC136188
0.8143	Intermediate Similarity	NPC130665
0.8143	Intermediate Similarity	NPC474140
0.8143	Intermediate Similarity	NPC474743
0.8143	Intermediate Similarity	NPC201373
0.8116	Intermediate Similarity	NPC475728
0.8082	Intermediate Similarity	NPC307965
0.8082	Intermediate Similarity	NPC76931
0.8082	Intermediate Similarity	NPC167891
0.8082	Intermediate Similarity	NPC18603
0.8082	Intermediate Similarity	NPC275910
0.8082	Intermediate Similarity	NPC186191
0.8082	Intermediate Similarity	NPC318136
0.8082	Intermediate Similarity	NPC205455
0.8082	Intermediate Similarity	NPC72507
0.8082	Intermediate Similarity	NPC83351
0.8056	Intermediate Similarity	NPC120098
0.8056	Intermediate Similarity	NPC247325
0.8056	Intermediate Similarity	NPC240604
0.8056	Intermediate Similarity	NPC122418
0.8056	Intermediate Similarity	NPC106364
0.8056	Intermediate Similarity	NPC300324
0.8056	Intermediate Similarity	NPC321381
0.8056	Intermediate Similarity	NPC189883
0.8056	Intermediate Similarity	NPC27765
0.8056	Intermediate Similarity	NPC321016
0.8056	Intermediate Similarity	NPC73875
0.8056	Intermediate Similarity	NPC244488
0.8056	Intermediate Similarity	NPC265328
0.8056	Intermediate Similarity	NPC107059
0.8056	Intermediate Similarity	NPC265588
0.8056	Intermediate Similarity	NPC30590
0.8056	Intermediate Similarity	NPC290598
0.803	Intermediate Similarity	NPC225415
0.8	Intermediate Similarity	NPC167706
0.7971	Intermediate Similarity	NPC474248
0.7945	Intermediate Similarity	NPC155986
0.7945	Intermediate Similarity	NPC90979
0.7945	Intermediate Similarity	NPC34177
0.7945	Intermediate Similarity	NPC34019
0.7945	Intermediate Similarity	NPC198968
0.7945	Intermediate Similarity	NPC40394
0.7945	Intermediate Similarity	NPC472805
0.7945	Intermediate Similarity	NPC101475
0.7945	Intermediate Similarity	NPC318495
0.7945	Intermediate Similarity	NPC130136
0.7945	Intermediate Similarity	NPC157996
0.7917	Intermediate Similarity	NPC477923
0.7917	Intermediate Similarity	NPC66566
0.791	Intermediate Similarity	NPC27243
0.791	Intermediate Similarity	NPC476737
0.7895	Intermediate Similarity	NPC87489
0.7887	Intermediate Similarity	NPC68443
0.7867	Intermediate Similarity	NPC164840
0.7867	Intermediate Similarity	NPC241290
0.7867	Intermediate Similarity	NPC209944
0.7867	Intermediate Similarity	NPC234193
0.7857	Intermediate Similarity	NPC92801
0.7838	Intermediate Similarity	NPC300499
0.7838	Intermediate Similarity	NPC473943
0.7838	Intermediate Similarity	NPC474216
0.7838	Intermediate Similarity	NPC477514
0.7838	Intermediate Similarity	NPC99168
0.7838	Intermediate Similarity	NPC22955
0.7838	Intermediate Similarity	NPC196753
0.7838	Intermediate Similarity	NPC230295
0.7838	Intermediate Similarity	NPC158662
0.7838	Intermediate Similarity	NPC477522
0.7838	Intermediate Similarity	NPC98386
0.7838	Intermediate Similarity	NPC470396
0.7838	Intermediate Similarity	NPC87604
0.7838	Intermediate Similarity	NPC474989
0.7838	Intermediate Similarity	NPC253807
0.7826	Intermediate Similarity	NPC96484
0.7826	Intermediate Similarity	NPC2648
0.7826	Intermediate Similarity	NPC94192
0.7808	Intermediate Similarity	NPC96319
0.7808	Intermediate Similarity	NPC477925
0.7808	Intermediate Similarity	NPC470749
0.7808	Intermediate Similarity	NPC274079
0.7808	Intermediate Similarity	NPC253190
0.7808	Intermediate Similarity	NPC237460
0.7794	Intermediate Similarity	NPC476406
0.7794	Intermediate Similarity	NPC202017
0.7794	Intermediate Similarity	NPC250977
0.7792	Intermediate Similarity	NPC470384
0.7792	Intermediate Similarity	NPC237795
0.7792	Intermediate Similarity	NPC82538
0.7778	Intermediate Similarity	NPC469534
0.7778	Intermediate Similarity	NPC469533
0.7778	Intermediate Similarity	NPC469593
0.7778	Intermediate Similarity	NPC179024
0.7778	Intermediate Similarity	NPC476366
0.7778	Intermediate Similarity	NPC201048
0.7763	Intermediate Similarity	NPC476646
0.7763	Intermediate Similarity	NPC6707
0.7763	Intermediate Similarity	NPC264245
0.7763	Intermediate Similarity	NPC47761
0.7761	Intermediate Similarity	NPC96793
0.7761	Intermediate Similarity	NPC323424
0.7761	Intermediate Similarity	NPC107540
0.7746	Intermediate Similarity	NPC164022
0.7733	Intermediate Similarity	NPC209430
0.7733	Intermediate Similarity	NPC100906
0.7733	Intermediate Similarity	NPC291379
0.7733	Intermediate Similarity	NPC28862
0.7733	Intermediate Similarity	NPC1319
0.7733	Intermediate Similarity	NPC84694
0.7733	Intermediate Similarity	NPC328714
0.7733	Intermediate Similarity	NPC53744
0.7733	Intermediate Similarity	NPC47982
0.7733	Intermediate Similarity	NPC30986
0.7733	Intermediate Similarity	NPC143182
0.7733	Intermediate Similarity	NPC109546
0.7733	Intermediate Similarity	NPC474113
0.7733	Intermediate Similarity	NPC81306
0.7727	Intermediate Similarity	NPC475251
0.7714	Intermediate Similarity	NPC210323
0.7714	Intermediate Similarity	NPC476431
0.7714	Intermediate Similarity	NPC473893
0.7703	Intermediate Similarity	NPC470758
0.7703	Intermediate Similarity	NPC470711
0.7703	Intermediate Similarity	NPC477924
0.7692	Intermediate Similarity	NPC238485
0.7692	Intermediate Similarity	NPC231310
0.7671	Intermediate Similarity	NPC171148
0.7671	Intermediate Similarity	NPC69383
0.7671	Intermediate Similarity	NPC32832
0.7671	Intermediate Similarity	NPC313179
0.7662	Intermediate Similarity	NPC50964
0.7662	Intermediate Similarity	NPC20853
0.7662	Intermediate Similarity	NPC49964
0.7662	Intermediate Similarity	NPC202389
0.7662	Intermediate Similarity	NPC73882
0.7662	Intermediate Similarity	NPC201852
0.7656	Intermediate Similarity	NPC11130
0.7632	Intermediate Similarity	NPC96362
0.7632	Intermediate Similarity	NPC295131
0.7632	Intermediate Similarity	NPC236112
0.7632	Intermediate Similarity	NPC2482
0.7632	Intermediate Similarity	NPC287749
0.7632	Intermediate Similarity	NPC26117
0.7612	Intermediate Similarity	NPC174956
0.7606	Intermediate Similarity	NPC9161
0.7606	Intermediate Similarity	NPC49422

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 NPC163678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	2130
0.2-0.3	4309
0.3-0.4	1850
0.4-0.5	408
0.5-0.6	217
0.6-0.7	68
0.7-0.8	15
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
0.8169	Intermediate Similarity	NPD7339	Approved
0.8169	Intermediate Similarity	NPD6942	Approved
0.7808	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4785	Approved
0.7778	Intermediate Similarity	NPD4784	Approved
0.7746	Intermediate Similarity	NPD4243	Approved
0.7733	Intermediate Similarity	NPD7645	Phase 2
0.7671	Intermediate Similarity	NPD8264	Approved
0.7606	Intermediate Similarity	NPD7144	Approved
0.7606	Intermediate Similarity	NPD7143	Approved
0.75	Intermediate Similarity	NPD7151	Approved
0.75	Intermediate Similarity	NPD7150	Approved
0.75	Intermediate Similarity	NPD7152	Approved
0.7465	Intermediate Similarity	NPD6922	Approved
0.7465	Intermediate Similarity	NPD6923	Approved
0.7403	Intermediate Similarity	NPD7525	Registered
0.7297	Intermediate Similarity	NPD6926	Approved
0.7297	Intermediate Similarity	NPD6924	Approved
0.725	Intermediate Similarity	NPD4786	Approved
0.7215	Intermediate Similarity	NPD3667	Approved
0.72	Intermediate Similarity	NPD5275	Approved
0.72	Intermediate Similarity	NPD4190	Phase 3
0.7179	Intermediate Similarity	NPD4748	Discontinued
0.7105	Intermediate Similarity	NPD6933	Approved
0.7077	Intermediate Similarity	NPD342	Phase 1
0.7051	Intermediate Similarity	NPD4195	Approved
0.7037	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD3665	Phase 1
0.7037	Intermediate Similarity	NPD3133	Approved
0.7013	Intermediate Similarity	NPD6932	Approved
0.697	Remote Similarity	NPD4219	Approved
0.6923	Remote Similarity	NPD7145	Approved
0.6923	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3618	Phase 1
0.6867	Remote Similarity	NPD5279	Phase 3
0.686	Remote Similarity	NPD6079	Approved
0.6835	Remote Similarity	NPD6929	Approved
0.6824	Remote Similarity	NPD5328	Approved
0.6795	Remote Similarity	NPD5776	Phase 2
0.6795	Remote Similarity	NPD6925	Approved
0.6786	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7514	Phase 3
0.675	Remote Similarity	NPD7332	Phase 2
0.675	Remote Similarity	NPD6931	Approved
0.675	Remote Similarity	NPD7509	Discontinued
0.675	Remote Similarity	NPD6930	Phase 2
0.6714	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6628	Remote Similarity	NPD4753	Phase 2
0.6625	Remote Similarity	NPD6683	Phase 2
0.6585	Remote Similarity	NPD4221	Approved
0.6585	Remote Similarity	NPD4223	Phase 3
0.6548	Remote Similarity	NPD5329	Approved
0.6543	Remote Similarity	NPD4695	Discontinued
0.6506	Remote Similarity	NPD6695	Phase 3
0.65	Remote Similarity	NPD3617	Approved
0.6477	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD5280	Approved
0.6471	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD4694	Approved
0.6471	Remote Similarity	NPD4519	Discontinued
0.6463	Remote Similarity	NPD4692	Approved
0.6463	Remote Similarity	NPD4139	Approved
0.6463	Remote Similarity	NPD6898	Phase 1
0.6444	Remote Similarity	NPD4629	Approved
0.6444	Remote Similarity	NPD5210	Approved
0.6437	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3668	Phase 3
0.6429	Remote Similarity	NPD4197	Approved
0.6429	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8262	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD4202	Approved
0.6374	Remote Similarity	NPD5222	Approved
0.6374	Remote Similarity	NPD5221	Approved
0.6374	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6893	Approved
0.6341	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7748	Approved
0.631	Remote Similarity	NPD4788	Approved
0.6304	Remote Similarity	NPD5173	Approved
0.6304	Remote Similarity	NPD6083	Phase 2
0.6304	Remote Similarity	NPD6084	Phase 2
0.6292	Remote Similarity	NPD5281	Approved
0.6292	Remote Similarity	NPD5284	Approved
0.6279	Remote Similarity	NPD4688	Approved
0.6279	Remote Similarity	NPD6409	Approved
0.6279	Remote Similarity	NPD7146	Approved
0.6279	Remote Similarity	NPD4690	Approved
0.6279	Remote Similarity	NPD5330	Approved
0.6279	Remote Similarity	NPD4693	Phase 3
0.6279	Remote Similarity	NPD7521	Approved
0.6279	Remote Similarity	NPD5205	Approved
0.6279	Remote Similarity	NPD6684	Approved
0.6279	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4138	Approved
0.6279	Remote Similarity	NPD7334	Approved
0.6279	Remote Similarity	NPD4689	Approved
0.6264	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6101	Approved
0.6237	Remote Similarity	NPD5290	Discontinued
0.623	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7750	Discontinued
0.6207	Remote Similarity	NPD7524	Approved
0.6203	Remote Similarity	NPD4687	Approved
0.6203	Remote Similarity	NPD5733	Approved
0.6196	Remote Similarity	NPD4697	Phase 3
0.6184	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5285	Approved
0.617	Remote Similarity	NPD5286	Approved
0.617	Remote Similarity	NPD4696	Approved
0.6163	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5737	Approved
0.6136	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6903	Approved
0.6136	Remote Similarity	NPD6672	Approved
0.6136	Remote Similarity	NPD4723	Approved
0.6136	Remote Similarity	NPD4722	Approved
0.6129	Remote Similarity	NPD4755	Approved
0.6129	Remote Similarity	NPD7902	Approved
0.6105	Remote Similarity	NPD5223	Approved
0.6104	Remote Similarity	NPD4137	Phase 3
0.6067	Remote Similarity	NPD6051	Approved
0.6064	Remote Similarity	NPD7638	Approved
0.6044	Remote Similarity	NPD5133	Approved
0.6042	Remote Similarity	NPD5211	Phase 2
0.6042	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD5224	Approved
0.6042	Remote Similarity	NPD5225	Approved
0.6042	Remote Similarity	NPD4633	Approved
0.6026	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4747	Approved
0.6026	Remote Similarity	NPD4691	Approved
0.6026	Remote Similarity	NPD6939	Phase 2
0.6022	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7136	Phase 2
0.6	Remote Similarity	NPD4058	Approved
0.6	Remote Similarity	NPD4096	Approved
0.6	Remote Similarity	NPD4700	Approved
0.5979	Remote Similarity	NPD5175	Approved
0.5979	Remote Similarity	NPD5174	Approved
0.5977	Remote Similarity	NPD1696	Phase 3
0.5955	Remote Similarity	NPD4518	Approved
0.5949	Remote Similarity	NPD5276	Approved
0.5934	Remote Similarity	NPD7087	Discontinued
0.5934	Remote Similarity	NPD7637	Suspended
0.5926	Remote Similarity	NPD8039	Approved
0.5921	Remote Similarity	NPD7331	Phase 2
0.5918	Remote Similarity	NPD5141	Approved
0.5909	Remote Similarity	NPD6098	Approved
0.5904	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6899	Approved
0.59	Remote Similarity	NPD6881	Approved
0.5897	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD15	Approved
0.5897	Remote Similarity	NPD791	Approved
0.5895	Remote Similarity	NPD5696	Approved
0.5875	Remote Similarity	NPD4732	Discontinued
0.587	Remote Similarity	NPD5779	Approved
0.587	Remote Similarity	NPD5778	Approved
0.5867	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD6402	Approved
0.5859	Remote Similarity	NPD7128	Approved
0.5859	Remote Similarity	NPD6675	Approved
0.5854	Remote Similarity	NPD1346	Approved
0.5846	Remote Similarity	NPD384	Approved
0.5846	Remote Similarity	NPD385	Approved
0.5843	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD6404	Discontinued
0.5824	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD5207	Approved
0.5823	Remote Similarity	NPD4787	Phase 1
0.5823	Remote Similarity	NPD4244	Approved
0.5823	Remote Similarity	NPD4245	Approved
0.5823	Remote Similarity	NPD4789	Approved
0.5816	Remote Similarity	NPD4754	Approved
0.5814	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD4192	Approved
0.5811	Remote Similarity	NPD4193	Approved
0.5811	Remote Similarity	NPD4191	Approved
0.5811	Remote Similarity	NPD4194	Approved
0.5806	Remote Similarity	NPD7900	Approved
0.5806	Remote Similarity	NPD5771	Approved
0.5806	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5697	Approved
0.58	Remote Similarity	NPD6412	Phase 2
0.5789	Remote Similarity	NPD7341	Phase 2
0.5789	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6883	Approved
0.5784	Remote Similarity	NPD7290	Approved
0.5784	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD6705	Phase 1
0.5761	Remote Similarity	NPD6050	Approved
0.5761	Remote Similarity	NPD5694	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