NPASS Compound

Structure

NPC197805 OpenBabel07101718322D 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 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 -2.5981 1.5000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 1 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 2 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 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 2 1 1 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	332.324
LogP:	4.995
LogD:	4.252
LogS:	-4.759
# 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:	0.7
Synthetic Accessibility Score:	4.561
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:	-4.595
MDCK Permeability:	1.6507992768310942e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	94.32654571533203%
Volume Distribution (VD):	0.875
Pgp-substrate:	4.066959857940674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.325
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.482

ADMET: Excretion

Clearance (CL):	5.362
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.306
Carcinogencity:	0.112
Eye Corrosion:	0.048
Eye Irritation:	0.559
Respiratory Toxicity:	0.708

Download Data

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

Natural Product: NPC197805

Natural Product ID:	NPC197805
*Common Name:**	Isopimara-7,15-Dien-19-Ol
IUPAC Name:	[(1S,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthren-1-yl]methanol
Synonyms:
Standard InCHIKey:	DUEINKIQNGZKPL-WKWVNEEDSA-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/h5,7,16-17,21H,1,6,8-14H2,2-4H3/t16-,17-,18-,19+,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2C(=CC[C@H]3[C@](C)(CCC[C@]23C)CO)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608620
PubChem CID:	158539
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
NPO33419	Sagittaria latifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26371504]
NPO33419	Sagittaria latifolia	Species	Alismataceae	Eukaryota		n.a.	n.a.	Database[FooDB]

☑ 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	4
MIC	2

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	37.5	ug.mL-1	PMID[549746]
NPT857	Cell Line	LLC-PK1	Sus scrofa	IC50	=	42.5	ug.mL-1	PMID[549746]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	20.0	ug.mL-1	PMID[549746]
NPT3665	Organism	Cryptococcus bacillisporus	Cryptococcus gattii	IC50	=	6.8	ug.mL-1	PMID[549746]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	9.2	ug.mL-1	PMID[549746]
NPT3665	Organism	Cryptococcus bacillisporus	Cryptococcus gattii	MIC	=	20.0	ug.mL-1	PMID[549746]

☑ 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 NPC197805 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	172
0.1-0.2	1532
0.2-0.3	9463
0.3-0.4	15364
0.4-0.5	7312
0.5-0.6	5455
0.6-0.7	2521
0.7-0.8	694
0.8-0.85	136
0.85-0.9	33
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC476039
0.9839	High Similarity	NPC222366
0.9839	High Similarity	NPC286669
0.9531	High Similarity	NPC32055
0.9365	High Similarity	NPC163678
0.9254	High Similarity	NPC471799
0.9254	High Similarity	NPC182717
0.9242	High Similarity	NPC145498
0.9231	High Similarity	NPC216460
0.9219	High Similarity	NPC149680
0.9118	High Similarity	NPC471797
0.9104	High Similarity	NPC242001
0.8939	High Similarity	NPC160209
0.8939	High Similarity	NPC208999
0.8857	High Similarity	NPC129165
0.8857	High Similarity	NPC113733
0.8857	High Similarity	NPC134330
0.8841	High Similarity	NPC477138
0.8841	High Similarity	NPC243342
0.8841	High Similarity	NPC100334
0.8841	High Similarity	NPC91858
0.8824	High Similarity	NPC110799
0.8788	High Similarity	NPC68703
0.8788	High Similarity	NPC69649
0.8732	High Similarity	NPC91594
0.8732	High Similarity	NPC471798
0.8714	High Similarity	NPC230301
0.8714	High Similarity	NPC291503
0.8714	High Similarity	NPC134847
0.8714	High Similarity	NPC141071
0.8714	High Similarity	NPC471468
0.8714	High Similarity	NPC162742
0.8714	High Similarity	NPC471723
0.8714	High Similarity	NPC257347
0.8714	High Similarity	NPC285893
0.8714	High Similarity	NPC22105
0.8714	High Similarity	NPC28657
0.8714	High Similarity	NPC288035
0.8714	High Similarity	NPC136188
0.8714	High Similarity	NPC304309
0.8696	High Similarity	NPC474743
0.8676	High Similarity	NPC475728
0.8676	High Similarity	NPC34834
0.8636	High Similarity	NPC279434
0.8611	High Similarity	NPC76931
0.8611	High Similarity	NPC307965
0.8611	High Similarity	NPC83351
0.8611	High Similarity	NPC18603
0.8611	High Similarity	NPC167891
0.8592	High Similarity	NPC321381
0.8592	High Similarity	NPC106364
0.8592	High Similarity	NPC27765
0.8592	High Similarity	NPC321016
0.8592	High Similarity	NPC240604
0.8592	High Similarity	NPC244488
0.8592	High Similarity	NPC265328
0.8592	High Similarity	NPC290598
0.8592	High Similarity	NPC189883
0.8592	High Similarity	NPC106432
0.8592	High Similarity	NPC30590
0.8592	High Similarity	NPC120098
0.8592	High Similarity	NPC122418
0.8592	High Similarity	NPC300324
0.8592	High Similarity	NPC247325
0.8592	High Similarity	NPC470362
0.8592	High Similarity	NPC107059
0.8551	High Similarity	NPC167706
0.8507	High Similarity	NPC171225
0.8485	Intermediate Similarity	NPC476737
0.8485	Intermediate Similarity	NPC27243
0.8472	Intermediate Similarity	NPC101475
0.8472	Intermediate Similarity	NPC90979
0.8472	Intermediate Similarity	NPC34019
0.8472	Intermediate Similarity	NPC40394
0.8472	Intermediate Similarity	NPC472805
0.8472	Intermediate Similarity	NPC155986
0.8472	Intermediate Similarity	NPC198968
0.8472	Intermediate Similarity	NPC34177
0.8472	Intermediate Similarity	NPC318495
0.8472	Intermediate Similarity	NPC157996
0.8472	Intermediate Similarity	NPC130136
0.8451	Intermediate Similarity	NPC34700
0.8451	Intermediate Similarity	NPC138374
0.8451	Intermediate Similarity	NPC477923
0.8451	Intermediate Similarity	NPC66566
0.8429	Intermediate Similarity	NPC68443
0.8429	Intermediate Similarity	NPC474140
0.8382	Intermediate Similarity	NPC94192
0.8378	Intermediate Similarity	NPC209944
0.8378	Intermediate Similarity	NPC234193
0.8378	Intermediate Similarity	NPC164840
0.8378	Intermediate Similarity	NPC241290
0.8358	Intermediate Similarity	NPC476406
0.8356	Intermediate Similarity	NPC474989
0.8356	Intermediate Similarity	NPC158662
0.8356	Intermediate Similarity	NPC196753
0.8356	Intermediate Similarity	NPC477522
0.8356	Intermediate Similarity	NPC87604
0.8356	Intermediate Similarity	NPC99168
0.8356	Intermediate Similarity	NPC474216
0.8356	Intermediate Similarity	NPC473943
0.8356	Intermediate Similarity	NPC98386
0.8356	Intermediate Similarity	NPC477514
0.8356	Intermediate Similarity	NPC253807
0.8356	Intermediate Similarity	NPC22955
0.8356	Intermediate Similarity	NPC300499
0.8356	Intermediate Similarity	NPC230295
0.8356	Intermediate Similarity	NPC470396
0.8333	Intermediate Similarity	NPC202642
0.8333	Intermediate Similarity	NPC237460
0.8333	Intermediate Similarity	NPC96319
0.8333	Intermediate Similarity	NPC253190
0.8333	Intermediate Similarity	NPC470749
0.8333	Intermediate Similarity	NPC290367
0.8333	Intermediate Similarity	NPC225415
0.8333	Intermediate Similarity	NPC265588
0.8333	Intermediate Similarity	NPC46160
0.8333	Intermediate Similarity	NPC274079
0.8333	Intermediate Similarity	NPC477925
0.831	Intermediate Similarity	NPC201048
0.831	Intermediate Similarity	NPC476366
0.831	Intermediate Similarity	NPC469534
0.831	Intermediate Similarity	NPC469593
0.831	Intermediate Similarity	NPC469533
0.8267	Intermediate Similarity	NPC47761
0.8267	Intermediate Similarity	NPC476646
0.8267	Intermediate Similarity	NPC264245
0.8261	Intermediate Similarity	NPC471560
0.8261	Intermediate Similarity	NPC474248
0.8261	Intermediate Similarity	NPC476431
0.8243	Intermediate Similarity	NPC328714
0.8243	Intermediate Similarity	NPC84694
0.8243	Intermediate Similarity	NPC1319
0.8243	Intermediate Similarity	NPC291379
0.8243	Intermediate Similarity	NPC109546
0.8243	Intermediate Similarity	NPC81306
0.8243	Intermediate Similarity	NPC143182
0.8243	Intermediate Similarity	NPC28862
0.8243	Intermediate Similarity	NPC53744
0.8243	Intermediate Similarity	NPC47982
0.8243	Intermediate Similarity	NPC30986
0.8243	Intermediate Similarity	NPC209430
0.8243	Intermediate Similarity	NPC100906
0.8235	Intermediate Similarity	NPC114651
0.8219	Intermediate Similarity	NPC470711
0.8219	Intermediate Similarity	NPC470758
0.8219	Intermediate Similarity	NPC214570
0.8219	Intermediate Similarity	NPC477924
0.8194	Intermediate Similarity	NPC121744
0.8194	Intermediate Similarity	NPC32832
0.8194	Intermediate Similarity	NPC118508
0.8194	Intermediate Similarity	NPC322353
0.8158	Intermediate Similarity	NPC50964
0.8158	Intermediate Similarity	NPC49964
0.8143	Intermediate Similarity	NPC92801
0.8133	Intermediate Similarity	NPC236112
0.8133	Intermediate Similarity	NPC295131
0.8133	Intermediate Similarity	NPC2482
0.8133	Intermediate Similarity	NPC287749
0.8133	Intermediate Similarity	NPC26117
0.8133	Intermediate Similarity	NPC96362
0.8116	Intermediate Similarity	NPC96484
0.8116	Intermediate Similarity	NPC2648
0.8108	Intermediate Similarity	NPC11908
0.8108	Intermediate Similarity	NPC138621
0.8108	Intermediate Similarity	NPC205455
0.8108	Intermediate Similarity	NPC72507
0.8108	Intermediate Similarity	NPC275910
0.8108	Intermediate Similarity	NPC85346
0.8108	Intermediate Similarity	NPC285761
0.8108	Intermediate Similarity	NPC186191
0.8108	Intermediate Similarity	NPC476314
0.8108	Intermediate Similarity	NPC318136
0.8108	Intermediate Similarity	NPC302041
0.8108	Intermediate Similarity	NPC65897
0.8108	Intermediate Similarity	NPC6978
0.8108	Intermediate Similarity	NPC167037
0.8108	Intermediate Similarity	NPC244385
0.8108	Intermediate Similarity	NPC312328
0.8088	Intermediate Similarity	NPC202017
0.8082	Intermediate Similarity	NPC73875
0.806	Intermediate Similarity	NPC107540
0.8056	Intermediate Similarity	NPC306727
0.8052	Intermediate Similarity	NPC82538
0.8052	Intermediate Similarity	NPC237795
0.803	Intermediate Similarity	NPC41160
0.8028	Intermediate Similarity	NPC164022
0.8026	Intermediate Similarity	NPC474531
0.8026	Intermediate Similarity	NPC142163
0.8026	Intermediate Similarity	NPC6434
0.8026	Intermediate Similarity	NPC7505
0.8026	Intermediate Similarity	NPC242350
0.8026	Intermediate Similarity	NPC209620
0.8026	Intermediate Similarity	NPC249423
0.8026	Intermediate Similarity	NPC474683
0.8026	Intermediate Similarity	NPC82986
0.8026	Intermediate Similarity	NPC3915
0.8026	Intermediate Similarity	NPC474752
0.8026	Intermediate Similarity	NPC474759
0.8026	Intermediate Similarity	NPC474731

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 NPC197805 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1800
0.2-0.3	4279
0.3-0.4	2062
0.4-0.5	482
0.5-0.6	196
0.6-0.7	122
0.7-0.8	36
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8714	High Similarity	NPD7339	Approved
0.8714	High Similarity	NPD6942	Approved
0.8333	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD4784	Approved
0.831	Intermediate Similarity	NPD4785	Approved
0.8286	Intermediate Similarity	NPD4243	Approved
0.8243	Intermediate Similarity	NPD7645	Phase 2
0.7895	Intermediate Similarity	NPD7525	Registered
0.7887	Intermediate Similarity	NPD7143	Approved
0.7887	Intermediate Similarity	NPD7144	Approved
0.7808	Intermediate Similarity	NPD6926	Approved
0.7808	Intermediate Similarity	NPD6924	Approved
0.7778	Intermediate Similarity	NPD7150	Approved
0.7778	Intermediate Similarity	NPD7152	Approved
0.7778	Intermediate Similarity	NPD7151	Approved
0.7746	Intermediate Similarity	NPD6922	Approved
0.7746	Intermediate Similarity	NPD6923	Approved
0.7722	Intermediate Similarity	NPD4786	Approved
0.7703	Intermediate Similarity	NPD5275	Approved
0.7703	Intermediate Similarity	NPD4190	Phase 3
0.7692	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD6933	Approved
0.7532	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.7467	Intermediate Similarity	NPD8264	Approved
0.7385	Intermediate Similarity	NPD342	Phase 1
0.7317	Intermediate Similarity	NPD3618	Phase 1
0.7308	Intermediate Similarity	NPD6929	Approved
0.7294	Intermediate Similarity	NPD6079	Approved
0.7273	Intermediate Similarity	NPD6932	Approved
0.7262	Intermediate Similarity	NPD5328	Approved
0.7229	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6931	Approved
0.7215	Intermediate Similarity	NPD6930	Phase 2
0.7215	Intermediate Similarity	NPD7509	Discontinued
0.7179	Intermediate Similarity	NPD7145	Approved
0.7179	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD4753	Phase 2
0.7051	Intermediate Similarity	NPD6925	Approved
0.7051	Intermediate Similarity	NPD5776	Phase 2
0.7037	Intermediate Similarity	NPD4223	Phase 3
0.7037	Intermediate Similarity	NPD4221	Approved
0.7015	Intermediate Similarity	NPD4219	Approved
0.7	Intermediate Similarity	NPD4748	Discontinued
0.7	Intermediate Similarity	NPD7332	Phase 2
0.7	Intermediate Similarity	NPD7514	Phase 3
0.7	Intermediate Similarity	NPD4695	Discontinued
0.6988	Remote Similarity	NPD5329	Approved
0.6951	Remote Similarity	NPD6695	Phase 3
0.6914	Remote Similarity	NPD6902	Approved
0.6905	Remote Similarity	NPD5279	Phase 3
0.6905	Remote Similarity	NPD4519	Discontinued
0.6905	Remote Similarity	NPD4623	Approved
0.6875	Remote Similarity	NPD6683	Phase 2
0.6867	Remote Similarity	NPD4197	Approved
0.6867	Remote Similarity	NPD3668	Phase 3
0.6867	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5210	Approved
0.6854	Remote Similarity	NPD4629	Approved
0.6818	Remote Similarity	NPD6399	Phase 3
0.6818	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD6893	Approved
0.6778	Remote Similarity	NPD5222	Approved
0.6778	Remote Similarity	NPD5221	Approved
0.6778	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD368	Approved
0.675	Remote Similarity	NPD3617	Approved
0.6747	Remote Similarity	NPD4788	Approved
0.6742	Remote Similarity	NPD7748	Approved
0.6707	Remote Similarity	NPD6898	Phase 1
0.6706	Remote Similarity	NPD4693	Phase 3
0.6706	Remote Similarity	NPD6684	Approved
0.6706	Remote Similarity	NPD4138	Approved
0.6706	Remote Similarity	NPD4688	Approved
0.6706	Remote Similarity	NPD7521	Approved
0.6706	Remote Similarity	NPD4689	Approved
0.6706	Remote Similarity	NPD5205	Approved
0.6706	Remote Similarity	NPD4690	Approved
0.6706	Remote Similarity	NPD5690	Phase 2
0.6706	Remote Similarity	NPD7334	Approved
0.6706	Remote Similarity	NPD6409	Approved
0.6706	Remote Similarity	NPD7146	Approved
0.6706	Remote Similarity	NPD5330	Approved
0.6703	Remote Similarity	NPD6084	Phase 2
0.6703	Remote Similarity	NPD6083	Phase 2
0.6703	Remote Similarity	NPD5173	Approved
0.663	Remote Similarity	NPD5290	Discontinued
0.6628	Remote Similarity	NPD7524	Approved
0.6628	Remote Similarity	NPD7750	Discontinued
0.6593	Remote Similarity	NPD4697	Phase 3
0.6588	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD5286	Approved
0.6559	Remote Similarity	NPD5285	Approved
0.6552	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4723	Approved
0.6552	Remote Similarity	NPD4722	Approved
0.6552	Remote Similarity	NPD6903	Approved
0.6552	Remote Similarity	NPD6672	Approved
0.6552	Remote Similarity	NPD5737	Approved
0.6522	Remote Similarity	NPD7902	Approved
0.6522	Remote Similarity	NPD4755	Approved
0.6517	Remote Similarity	NPD6411	Approved
0.6512	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4694	Approved
0.6512	Remote Similarity	NPD5280	Approved
0.6489	Remote Similarity	NPD5223	Approved
0.6477	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6051	Approved
0.6452	Remote Similarity	NPD7638	Approved
0.6447	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5224	Approved
0.6421	Remote Similarity	NPD5211	Phase 2
0.6421	Remote Similarity	NPD4633	Approved
0.6421	Remote Similarity	NPD5225	Approved
0.6421	Remote Similarity	NPD5226	Approved
0.6383	Remote Similarity	NPD7639	Approved
0.6383	Remote Similarity	NPD7640	Approved
0.6383	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD4137	Phase 3
0.6354	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD5175	Approved
0.6333	Remote Similarity	NPD7087	Discontinued
0.6333	Remote Similarity	NPD5284	Approved
0.6333	Remote Similarity	NPD5281	Approved
0.6322	Remote Similarity	NPD6098	Approved
0.631	Remote Similarity	NPD4139	Approved
0.631	Remote Similarity	NPD4692	Approved
0.6304	Remote Similarity	NPD5695	Phase 3
0.6292	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6101	Approved
0.629	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5141	Approved
0.6282	Remote Similarity	NPD4691	Approved
0.6282	Remote Similarity	NPD4747	Approved
0.6282	Remote Similarity	NPD6939	Phase 2
0.6282	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5696	Approved
0.6263	Remote Similarity	NPD6899	Approved
0.6263	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD4058	Approved
0.625	Remote Similarity	NPD3573	Approved
0.6235	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6675	Approved
0.6224	Remote Similarity	NPD5739	Approved
0.6224	Remote Similarity	NPD6402	Approved
0.6224	Remote Similarity	NPD7128	Approved
0.6222	Remote Similarity	NPD7136	Phase 2
0.6212	Remote Similarity	NPD8262	Approved
0.6196	Remote Similarity	NPD7900	Approved
0.6196	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4754	Approved
0.6162	Remote Similarity	NPD6412	Phase 2
0.6162	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7637	Suspended
0.6139	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD7290	Approved
0.6139	Remote Similarity	NPD6883	Approved
0.6111	Remote Similarity	NPD6673	Approved
0.6111	Remote Similarity	NPD6080	Approved
0.6111	Remote Similarity	NPD6904	Approved
0.61	Remote Similarity	NPD4729	Approved
0.61	Remote Similarity	NPD5168	Approved
0.61	Remote Similarity	NPD4730	Approved
0.61	Remote Similarity	NPD6011	Approved
0.61	Remote Similarity	NPD7320	Approved
0.6098	Remote Similarity	NPD1346	Approved
0.6078	Remote Similarity	NPD6650	Approved
0.6078	Remote Similarity	NPD6649	Approved
0.6078	Remote Similarity	NPD6869	Approved
0.6078	Remote Similarity	NPD6847	Approved
0.6078	Remote Similarity	NPD8130	Phase 1
0.6078	Remote Similarity	NPD6617	Approved
0.6076	Remote Similarity	NPD4787	Phase 1
0.6076	Remote Similarity	NPD4245	Approved
0.6076	Remote Similarity	NPD4244	Approved
0.6076	Remote Similarity	NPD4789	Approved
0.6064	Remote Similarity	NPD7614	Phase 1
0.6061	Remote Similarity	NPD4767	Approved
0.6061	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4687	Approved
0.6049	Remote Similarity	NPD5733	Approved
0.6044	Remote Similarity	NPD4096	Approved
0.604	Remote Similarity	NPD6014	Approved
0.604	Remote Similarity	NPD6012	Approved
0.604	Remote Similarity	NPD6373	Approved
0.604	Remote Similarity	NPD6372	Approved
0.604	Remote Similarity	NPD6013	Approved
0.6026	Remote Similarity	NPD6705	Phase 1
0.6022	Remote Similarity	NPD5771	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD5208	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