NPASS Compound

Structure

CID222366 OpenBabel06191716012D 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 3 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 3 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 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 2 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 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 2 1 1 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:	4.477
LogD:	3.638
LogS:	-5.382
# 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:	4.509
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:	-4.712
MDCK Permeability:	1.2777371011907235e-05
Pgp-inhibitor:	0.22
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.909
Plasma Protein Binding (PPB):	98.27179718017578%
Volume Distribution (VD):	1.888
Pgp-substrate:	2.4182584285736084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.52
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.33
CYP2D6-inhibitor:	0.347
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.887
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	4.249
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.463
Carcinogencity:	0.096
Eye Corrosion:	0.069
Eye Irritation:	0.675
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC222366

Natural Product ID:	NPC222366
*Common Name:**	Acanthol
IUPAC Name:	[(1R,4aR,7S)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthren-1-yl]methanol
Synonyms:	Acanthol
Standard InCHIKey:	YSFNIVKHYKBKHI-SAETXWKOSA-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/h5,9,15,17,21H,1,6-8,10-14H2,2-4H3/t15?,17?,18-,19-,20-/m0/s1
SMILES:	C=C[C@@]1(C)CC=C2C(CCC3[C@@](C)(CCC[C@@]23C)CO)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL115590
PubChem CID:	9882419
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
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20621475]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	steamed leaves	n.a.	n.a.	PMID[20932756]
NPO29834	Acanthopanax koreanum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25047	Eleutherococcus koreanus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	84.8	%	PMID[511090]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	>	1000000.0	nM	PMID[511091]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	791100.0	nM	PMID[511091]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[511092]

☑ 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 NPC222366 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	169
0.1-0.2	1532
0.2-0.3	10210
0.3-0.4	14906
0.4-0.5	7441
0.5-0.6	5336
0.6-0.7	2382
0.7-0.8	582
0.8-0.85	104
0.85-0.9	22
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC286669
1.0	High Similarity	NPC476039
0.9839	High Similarity	NPC197805
0.9516	High Similarity	NPC163678
0.9375	High Similarity	NPC32055
0.9104	High Similarity	NPC182717
0.9104	High Similarity	NPC471799
0.9091	High Similarity	NPC145498
0.9077	High Similarity	NPC216460
0.9062	High Similarity	NPC149680
0.8971	High Similarity	NPC471797
0.8955	High Similarity	NPC242001
0.8788	High Similarity	NPC208999
0.8788	High Similarity	NPC160209
0.8714	High Similarity	NPC113733
0.8714	High Similarity	NPC129165
0.8714	High Similarity	NPC134330
0.8696	High Similarity	NPC477138
0.8696	High Similarity	NPC243342
0.8696	High Similarity	NPC100334
0.8696	High Similarity	NPC91858
0.8676	High Similarity	NPC110799
0.8636	High Similarity	NPC69649
0.8636	High Similarity	NPC68703
0.8592	High Similarity	NPC91594
0.8592	High Similarity	NPC471798
0.8571	High Similarity	NPC22105
0.8571	High Similarity	NPC230301
0.8571	High Similarity	NPC285893
0.8571	High Similarity	NPC28657
0.8571	High Similarity	NPC304309
0.8571	High Similarity	NPC471468
0.8571	High Similarity	NPC136188
0.8571	High Similarity	NPC134847
0.8571	High Similarity	NPC291503
0.8571	High Similarity	NPC162742
0.8571	High Similarity	NPC141071
0.8571	High Similarity	NPC257347
0.8571	High Similarity	NPC471723
0.8571	High Similarity	NPC288035
0.8551	High Similarity	NPC474743
0.8529	High Similarity	NPC475728
0.8529	High Similarity	NPC34834
0.8485	Intermediate Similarity	NPC279434
0.8472	Intermediate Similarity	NPC307965
0.8472	Intermediate Similarity	NPC76931
0.8472	Intermediate Similarity	NPC18603
0.8472	Intermediate Similarity	NPC83351
0.8472	Intermediate Similarity	NPC167891
0.8462	Intermediate Similarity	NPC290367
0.8451	Intermediate Similarity	NPC240604
0.8451	Intermediate Similarity	NPC27765
0.8451	Intermediate Similarity	NPC120098
0.8451	Intermediate Similarity	NPC122418
0.8451	Intermediate Similarity	NPC247325
0.8451	Intermediate Similarity	NPC106432
0.8451	Intermediate Similarity	NPC244488
0.8451	Intermediate Similarity	NPC321016
0.8451	Intermediate Similarity	NPC300324
0.8451	Intermediate Similarity	NPC470362
0.8451	Intermediate Similarity	NPC106364
0.8451	Intermediate Similarity	NPC265328
0.8451	Intermediate Similarity	NPC189883
0.8451	Intermediate Similarity	NPC107059
0.8451	Intermediate Similarity	NPC290598
0.8451	Intermediate Similarity	NPC30590
0.8451	Intermediate Similarity	NPC321381
0.8406	Intermediate Similarity	NPC167706
0.8358	Intermediate Similarity	NPC114651
0.8358	Intermediate Similarity	NPC171225
0.8333	Intermediate Similarity	NPC130136
0.8333	Intermediate Similarity	NPC34019
0.8333	Intermediate Similarity	NPC472805
0.8333	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC476737
0.8333	Intermediate Similarity	NPC198968
0.8333	Intermediate Similarity	NPC27243
0.8333	Intermediate Similarity	NPC34177
0.8333	Intermediate Similarity	NPC318495
0.8333	Intermediate Similarity	NPC40394
0.8333	Intermediate Similarity	NPC157996
0.8333	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC90979
0.831	Intermediate Similarity	NPC34700
0.831	Intermediate Similarity	NPC138374
0.831	Intermediate Similarity	NPC66566
0.831	Intermediate Similarity	NPC477923
0.8286	Intermediate Similarity	NPC68443
0.8286	Intermediate Similarity	NPC474140
0.8243	Intermediate Similarity	NPC209944
0.8243	Intermediate Similarity	NPC241290
0.8243	Intermediate Similarity	NPC164840
0.8243	Intermediate Similarity	NPC234193
0.8235	Intermediate Similarity	NPC94192
0.8219	Intermediate Similarity	NPC98386
0.8219	Intermediate Similarity	NPC158662
0.8219	Intermediate Similarity	NPC87604
0.8219	Intermediate Similarity	NPC474989
0.8219	Intermediate Similarity	NPC99168
0.8219	Intermediate Similarity	NPC473943
0.8219	Intermediate Similarity	NPC470396
0.8219	Intermediate Similarity	NPC22955
0.8219	Intermediate Similarity	NPC474216
0.8219	Intermediate Similarity	NPC253807
0.8219	Intermediate Similarity	NPC477522
0.8219	Intermediate Similarity	NPC477514
0.8219	Intermediate Similarity	NPC300499
0.8219	Intermediate Similarity	NPC230295
0.8219	Intermediate Similarity	NPC196753
0.8209	Intermediate Similarity	NPC476406
0.8194	Intermediate Similarity	NPC253190
0.8194	Intermediate Similarity	NPC237460
0.8194	Intermediate Similarity	NPC202642
0.8194	Intermediate Similarity	NPC96319
0.8194	Intermediate Similarity	NPC470749
0.8194	Intermediate Similarity	NPC46160
0.8194	Intermediate Similarity	NPC274079
0.8194	Intermediate Similarity	NPC477925
0.8194	Intermediate Similarity	NPC265588
0.8182	Intermediate Similarity	NPC225415
0.8169	Intermediate Similarity	NPC201048
0.8169	Intermediate Similarity	NPC469533
0.8169	Intermediate Similarity	NPC469534
0.8169	Intermediate Similarity	NPC476366
0.8169	Intermediate Similarity	NPC469593
0.8133	Intermediate Similarity	NPC47761
0.8133	Intermediate Similarity	NPC264245
0.8133	Intermediate Similarity	NPC476646
0.8116	Intermediate Similarity	NPC476431
0.8116	Intermediate Similarity	NPC471560
0.8116	Intermediate Similarity	NPC474248
0.8108	Intermediate Similarity	NPC47982
0.8108	Intermediate Similarity	NPC1319
0.8108	Intermediate Similarity	NPC81306
0.8108	Intermediate Similarity	NPC291379
0.8108	Intermediate Similarity	NPC30986
0.8108	Intermediate Similarity	NPC143182
0.8108	Intermediate Similarity	NPC109546
0.8108	Intermediate Similarity	NPC84694
0.8108	Intermediate Similarity	NPC328714
0.8108	Intermediate Similarity	NPC209430
0.8108	Intermediate Similarity	NPC53744
0.8108	Intermediate Similarity	NPC100906
0.8108	Intermediate Similarity	NPC28862
0.8082	Intermediate Similarity	NPC477924
0.8082	Intermediate Similarity	NPC470758
0.8082	Intermediate Similarity	NPC214570
0.8082	Intermediate Similarity	NPC470711
0.8056	Intermediate Similarity	NPC118508
0.8056	Intermediate Similarity	NPC32832
0.8056	Intermediate Similarity	NPC121744
0.8056	Intermediate Similarity	NPC322353
0.8026	Intermediate Similarity	NPC49964
0.8026	Intermediate Similarity	NPC50964
0.8	Intermediate Similarity	NPC287749
0.8	Intermediate Similarity	NPC92801
0.8	Intermediate Similarity	NPC2482
0.8	Intermediate Similarity	NPC96362
0.8	Intermediate Similarity	NPC295131
0.8	Intermediate Similarity	NPC49422
0.8	Intermediate Similarity	NPC9161
0.8	Intermediate Similarity	NPC236112
0.8	Intermediate Similarity	NPC26117
0.7973	Intermediate Similarity	NPC302041
0.7973	Intermediate Similarity	NPC65897
0.7973	Intermediate Similarity	NPC244385
0.7973	Intermediate Similarity	NPC205455
0.7973	Intermediate Similarity	NPC312328
0.7973	Intermediate Similarity	NPC85346
0.7973	Intermediate Similarity	NPC6978
0.7973	Intermediate Similarity	NPC72507
0.7973	Intermediate Similarity	NPC138621
0.7973	Intermediate Similarity	NPC476314
0.7973	Intermediate Similarity	NPC167037
0.7973	Intermediate Similarity	NPC318136
0.7973	Intermediate Similarity	NPC285761
0.7973	Intermediate Similarity	NPC275910
0.7973	Intermediate Similarity	NPC11908
0.7973	Intermediate Similarity	NPC186191
0.7971	Intermediate Similarity	NPC2648
0.7971	Intermediate Similarity	NPC96484
0.7945	Intermediate Similarity	NPC73875
0.7941	Intermediate Similarity	NPC202017
0.7941	Intermediate Similarity	NPC250977
0.7922	Intermediate Similarity	NPC237795
0.7922	Intermediate Similarity	NPC82538
0.7917	Intermediate Similarity	NPC476046
0.7917	Intermediate Similarity	NPC251970
0.7917	Intermediate Similarity	NPC306727
0.7917	Intermediate Similarity	NPC241854
0.791	Intermediate Similarity	NPC96793
0.791	Intermediate Similarity	NPC107540
0.791	Intermediate Similarity	NPC323424
0.7895	Intermediate Similarity	NPC474531
0.7895	Intermediate Similarity	NPC470383
0.7895	Intermediate Similarity	NPC3915
0.7895	Intermediate Similarity	NPC249423
0.7895	Intermediate Similarity	NPC6434
0.7895	Intermediate Similarity	NPC82986
0.7895	Intermediate Similarity	NPC474752

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 NPC222366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1800
0.2-0.3	4329
0.3-0.4	2040
0.4-0.5	465
0.5-0.6	205
0.6-0.7	113
0.7-0.8	33
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7339	Approved
0.8571	High Similarity	NPD6942	Approved
0.8194	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4785	Approved
0.8169	Intermediate Similarity	NPD4784	Approved
0.8143	Intermediate Similarity	NPD4243	Approved
0.8108	Intermediate Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD7144	Approved
0.8	Intermediate Similarity	NPD7143	Approved
0.7887	Intermediate Similarity	NPD7152	Approved
0.7887	Intermediate Similarity	NPD7150	Approved
0.7887	Intermediate Similarity	NPD7151	Approved
0.7857	Intermediate Similarity	NPD6922	Approved
0.7857	Intermediate Similarity	NPD6923	Approved
0.7763	Intermediate Similarity	NPD7525	Registered
0.7671	Intermediate Similarity	NPD6924	Approved
0.7671	Intermediate Similarity	NPD6926	Approved
0.7595	Intermediate Similarity	NPD4786	Approved
0.7568	Intermediate Similarity	NPD8264	Approved
0.7568	Intermediate Similarity	NPD5275	Approved
0.7568	Intermediate Similarity	NPD4190	Phase 3
0.7564	Intermediate Similarity	NPD3667	Approved
0.7467	Intermediate Similarity	NPD6933	Approved
0.7403	Intermediate Similarity	NPD4195	Approved
0.7375	Intermediate Similarity	NPD3133	Approved
0.7375	Intermediate Similarity	NPD3666	Approved
0.7375	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD6932	Approved
0.7273	Intermediate Similarity	NPD7145	Approved
0.7273	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD342	Phase 1
0.7195	Intermediate Similarity	NPD3618	Phase 1
0.7179	Intermediate Similarity	NPD6929	Approved
0.7176	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD6925	Approved
0.7143	Intermediate Similarity	NPD5776	Phase 2
0.7121	Intermediate Similarity	NPD4219	Approved
0.7108	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7514	Phase 3
0.7089	Intermediate Similarity	NPD7332	Phase 2
0.7089	Intermediate Similarity	NPD6930	Phase 2
0.7089	Intermediate Similarity	NPD7509	Discontinued
0.7089	Intermediate Similarity	NPD6931	Approved
0.7	Intermediate Similarity	NPD6902	Approved
0.6977	Remote Similarity	NPD7515	Phase 2
0.6962	Remote Similarity	NPD6683	Phase 2
0.6941	Remote Similarity	NPD4753	Phase 2
0.6914	Remote Similarity	NPD4221	Approved
0.6914	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD4748	Discontinued
0.6875	Remote Similarity	NPD4695	Discontinued
0.6867	Remote Similarity	NPD5329	Approved
0.6857	Remote Similarity	NPD368	Approved
0.6829	Remote Similarity	NPD6695	Phase 3
0.679	Remote Similarity	NPD6898	Phase 1
0.6786	Remote Similarity	NPD4623	Approved
0.6786	Remote Similarity	NPD5279	Phase 3
0.6786	Remote Similarity	NPD4519	Discontinued
0.6747	Remote Similarity	NPD4197	Approved
0.6747	Remote Similarity	NPD3668	Phase 3
0.6747	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5210	Approved
0.6742	Remote Similarity	NPD4629	Approved
0.6705	Remote Similarity	NPD4202	Approved
0.6705	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6629	Remote Similarity	NPD7748	Approved
0.6627	Remote Similarity	NPD4788	Approved
0.6625	Remote Similarity	NPD3617	Approved
0.6593	Remote Similarity	NPD6083	Phase 2
0.6593	Remote Similarity	NPD5173	Approved
0.6593	Remote Similarity	NPD6084	Phase 2
0.6588	Remote Similarity	NPD7521	Approved
0.6588	Remote Similarity	NPD5690	Phase 2
0.6588	Remote Similarity	NPD7334	Approved
0.6588	Remote Similarity	NPD7146	Approved
0.6588	Remote Similarity	NPD4690	Approved
0.6588	Remote Similarity	NPD6409	Approved
0.6588	Remote Similarity	NPD6684	Approved
0.6588	Remote Similarity	NPD5330	Approved
0.6588	Remote Similarity	NPD4693	Phase 3
0.6588	Remote Similarity	NPD4688	Approved
0.6588	Remote Similarity	NPD5205	Approved
0.6588	Remote Similarity	NPD4138	Approved
0.6588	Remote Similarity	NPD4689	Approved
0.6533	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5290	Discontinued
0.6512	Remote Similarity	NPD7750	Discontinued
0.6512	Remote Similarity	NPD7524	Approved
0.6484	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5286	Approved
0.6452	Remote Similarity	NPD4696	Approved
0.6452	Remote Similarity	NPD5285	Approved
0.6447	Remote Similarity	NPD4137	Phase 3
0.6437	Remote Similarity	NPD5737	Approved
0.6437	Remote Similarity	NPD4723	Approved
0.6437	Remote Similarity	NPD6903	Approved
0.6437	Remote Similarity	NPD6672	Approved
0.6437	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4722	Approved
0.6413	Remote Similarity	NPD4755	Approved
0.6413	Remote Similarity	NPD7902	Approved
0.6404	Remote Similarity	NPD6411	Approved
0.6395	Remote Similarity	NPD5280	Approved
0.6395	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4694	Approved
0.6393	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD4691	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4747	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6939	Phase 2
0.6344	Remote Similarity	NPD7638	Approved
0.6329	Remote Similarity	NPD4058	Approved
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6316	Remote Similarity	NPD5211	Phase 2
0.6308	Remote Similarity	NPD8262	Approved
0.6292	Remote Similarity	NPD7136	Phase 2
0.6277	Remote Similarity	NPD4700	Approved
0.6277	Remote Similarity	NPD7640	Approved
0.6277	Remote Similarity	NPD7639	Approved
0.6265	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6222	Remote Similarity	NPD7087	Discontinued
0.6222	Remote Similarity	NPD5284	Approved
0.6222	Remote Similarity	NPD7637	Suspended
0.6222	Remote Similarity	NPD5281	Approved
0.6207	Remote Similarity	NPD6098	Approved
0.6196	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD4139	Approved
0.619	Remote Similarity	NPD4692	Approved
0.6186	Remote Similarity	NPD5141	Approved
0.618	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6101	Approved
0.617	Remote Similarity	NPD5696	Approved
0.6162	Remote Similarity	NPD6899	Approved
0.6162	Remote Similarity	NPD6881	Approved
0.6136	Remote Similarity	NPD3573	Approved
0.6125	Remote Similarity	NPD5733	Approved
0.6125	Remote Similarity	NPD4687	Approved
0.6122	Remote Similarity	NPD6675	Approved
0.6122	Remote Similarity	NPD5739	Approved
0.6122	Remote Similarity	NPD7128	Approved
0.6122	Remote Similarity	NPD6402	Approved
0.6118	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7900	Approved
0.6087	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4754	Approved
0.6061	Remote Similarity	NPD5697	Approved
0.6061	Remote Similarity	NPD6412	Phase 2
0.6053	Remote Similarity	NPD7331	Phase 2
0.6049	Remote Similarity	NPD8039	Approved
0.604	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD6883	Approved
0.604	Remote Similarity	NPD7290	Approved
0.6026	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD791	Approved
0.6026	Remote Similarity	NPD15	Approved
0.6024	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD4732	Discontinued
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5168	Approved
0.6	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD8130	Phase 1
0.598	Remote Similarity	NPD6617	Approved
0.598	Remote Similarity	NPD6869	Approved
0.598	Remote Similarity	NPD6650	Approved
0.598	Remote Similarity	NPD6847	Approved
0.598	Remote Similarity	NPD6649	Approved
0.5976	Remote Similarity	NPD1346	Approved
0.596	Remote Similarity	NPD4768	Approved
0.596	Remote Similarity	NPD4767	Approved
0.5957	Remote Similarity	NPD7614	Phase 1
0.5949	Remote Similarity	NPD4245	Approved
0.5949	Remote Similarity	NPD4244	Approved
0.5949	Remote Similarity	NPD4789	Approved
0.5949	Remote Similarity	NPD4787	Phase 1
0.5946	Remote Similarity	NPD4192	Approved
0.5946	Remote Similarity	NPD4193	Approved
0.5946	Remote Similarity	NPD4191	Approved
0.5946	Remote Similarity	NPD4194	Approved
0.5941	Remote Similarity	NPD6012	Approved
0.5941	Remote Similarity	NPD6013	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