NPASS Compound

Structure

NPC469728 OpenBabel07101718312D 21 22 0 0 1 0 0 0 0 0999 V2000 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -5.3660 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 -1.7321 -3.0000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 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 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 16 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 8 1 0 0 0 0 6 11 2 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 16 18 1 0 0 0 0 17 15 1 1 0 0 0 18 20 1 1 0 0 0 19 21 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	4.314
LogD:	3.666
LogS:	-4.106
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	4.787
Fsp3:	0.6
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:	-4.529
MDCK Permeability:	1.7990254491451196e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	92.84349822998047%
Volume Distribution (VD):	1.206
Pgp-substrate:	6.572417736053467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.157
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.649
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.603
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	4.033
Half-life (T1/2):	0.372

ADMET: Toxicity

hERG Blockers:	0.331
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.953
Carcinogencity:	0.91
Eye Corrosion:	0.029
Eye Irritation:	0.661
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC469728

Natural Product ID:	NPC469728
*Common Name:**	Gyrosanol B
IUPAC Name:	(3E)-6-[(2S,4aR,8aR)-4a,8-dimethyl-2,3,4,8a-tetrahydro-1H-naphthalen-2-yl]-2-methylhepta-3,6-dien-2-ol
Synonyms:	gyrosanol B
Standard InCHIKey:	MTVZOJVTVZWEBK-RNSWOICUSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-15(8-6-11-19(3,4)21)17-10-13-20(5)12-7-9-16(2)18(20)14-17/h6-7,9,11-12,17-18,21H,1,8,10,13-14H2,2-5H3/b11-6+/t17-,18+,20-/m0/s1
SMILES:	C=C([C@H]1CC[C@]2([C@H](C1)C(=CC=C2)C)C)C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163885
PubChem CID:	46906458
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
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23707	Sinularia gyrosa	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
IC50	1
Others	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	29.1	%	PMID[517609]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	171.7	%	PMID[517609]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	3700.0	nM	PMID[517609]

☑ 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 NPC469728 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	150
0.1-0.2	1984
0.2-0.3	12122
0.3-0.4	15788
0.4-0.5	7988
0.5-0.6	3654
0.6-0.7	901
0.7-0.8	102
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC176621
0.8438	Intermediate Similarity	NPC279434
0.8254	Intermediate Similarity	NPC174956
0.8167	Intermediate Similarity	NPC55412
0.8167	Intermediate Similarity	NPC249645
0.8033	Intermediate Similarity	NPC11130
0.7969	Intermediate Similarity	NPC81615
0.7879	Intermediate Similarity	NPC259156
0.7879	Intermediate Similarity	NPC242945
0.7879	Intermediate Similarity	NPC255781
0.7794	Intermediate Similarity	NPC476431
0.7714	Intermediate Similarity	NPC130665
0.7681	Intermediate Similarity	NPC34834
0.7586	Intermediate Similarity	NPC17518
0.7538	Intermediate Similarity	NPC41160
0.7538	Intermediate Similarity	NPC317025
0.7538	Intermediate Similarity	NPC326645
0.7538	Intermediate Similarity	NPC317177
0.7538	Intermediate Similarity	NPC329416
0.7536	Intermediate Similarity	NPC471560
0.7536	Intermediate Similarity	NPC474248
0.75	Intermediate Similarity	NPC476346
0.75	Intermediate Similarity	NPC114651
0.75	Intermediate Similarity	NPC208638
0.75	Intermediate Similarity	NPC171148
0.75	Intermediate Similarity	NPC69383
0.75	Intermediate Similarity	NPC313179
0.75	Intermediate Similarity	NPC171225
0.75	Intermediate Similarity	NPC309825
0.7465	Intermediate Similarity	NPC130016
0.7465	Intermediate Similarity	NPC109576
0.7465	Intermediate Similarity	NPC180015
0.7465	Intermediate Similarity	NPC56747
0.7463	Intermediate Similarity	NPC107258
0.7429	Intermediate Similarity	NPC475728
0.7414	Intermediate Similarity	NPC124851
0.7397	Intermediate Similarity	NPC265588
0.7391	Intermediate Similarity	NPC216460
0.7391	Intermediate Similarity	NPC32055
0.7391	Intermediate Similarity	NPC96484
0.7368	Intermediate Similarity	NPC86683
0.7361	Intermediate Similarity	NPC201048
0.7361	Intermediate Similarity	NPC476366
0.7353	Intermediate Similarity	NPC250977
0.7353	Intermediate Similarity	NPC476039
0.7353	Intermediate Similarity	NPC222366
0.7353	Intermediate Similarity	NPC286669
0.7353	Intermediate Similarity	NPC149680
0.7353	Intermediate Similarity	NPC202017
0.7344	Intermediate Similarity	NPC60772
0.7344	Intermediate Similarity	NPC469769
0.7313	Intermediate Similarity	NPC96793
0.7313	Intermediate Similarity	NPC323424
0.7313	Intermediate Similarity	NPC469662
0.7308	Intermediate Similarity	NPC231310
0.7308	Intermediate Similarity	NPC238485
0.7302	Intermediate Similarity	NPC179024
0.7302	Intermediate Similarity	NPC39068
0.7297	Intermediate Similarity	NPC91594
0.7297	Intermediate Similarity	NPC91665
0.7288	Intermediate Similarity	NPC22765
0.7286	Intermediate Similarity	NPC473893
0.7273	Intermediate Similarity	NPC79576
0.7273	Intermediate Similarity	NPC282694
0.7273	Intermediate Similarity	NPC194208
0.726	Intermediate Similarity	NPC32832
0.7246	Intermediate Similarity	NPC68703
0.7246	Intermediate Similarity	NPC69649
0.7246	Intermediate Similarity	NPC197805
0.7213	Intermediate Similarity	NPC35519
0.7213	Intermediate Similarity	NPC306195
0.7213	Intermediate Similarity	NPC157781
0.7213	Intermediate Similarity	NPC181255
0.7213	Intermediate Similarity	NPC179169
0.7213	Intermediate Similarity	NPC68014
0.7206	Intermediate Similarity	NPC163678
0.7206	Intermediate Similarity	NPC64123
0.72	Intermediate Similarity	NPC179028
0.72	Intermediate Similarity	NPC275494
0.72	Intermediate Similarity	NPC167891
0.72	Intermediate Similarity	NPC471409
0.72	Intermediate Similarity	NPC83351
0.7183	Intermediate Similarity	NPC189745
0.7179	Intermediate Similarity	NPC470384
0.7164	Intermediate Similarity	NPC202118
0.7164	Intermediate Similarity	NPC197238
0.7164	Intermediate Similarity	NPC283247
0.7162	Intermediate Similarity	NPC244488
0.7162	Intermediate Similarity	NPC253190
0.7162	Intermediate Similarity	NPC247325
0.7162	Intermediate Similarity	NPC470749
0.7143	Intermediate Similarity	NPC94192
0.7143	Intermediate Similarity	NPC6663
0.7143	Intermediate Similarity	NPC310992
0.7143	Intermediate Similarity	NPC208999
0.7143	Intermediate Similarity	NPC4166
0.7143	Intermediate Similarity	NPC264245
0.7121	Intermediate Similarity	NPC135648
0.7105	Intermediate Similarity	NPC170394
0.7101	Intermediate Similarity	NPC176171
0.7101	Intermediate Similarity	NPC92327
0.7101	Intermediate Similarity	NPC476406
0.7083	Intermediate Similarity	NPC133253
0.7083	Intermediate Similarity	NPC23954
0.7083	Intermediate Similarity	NPC95863
0.7083	Intermediate Similarity	NPC470078
0.7067	Intermediate Similarity	NPC470711
0.7067	Intermediate Similarity	NPC470758
0.7067	Intermediate Similarity	NPC132542
0.7059	Intermediate Similarity	NPC107540
0.7051	Intermediate Similarity	NPC49964
0.7051	Intermediate Similarity	NPC469804
0.7051	Intermediate Similarity	NPC87489
0.7051	Intermediate Similarity	NPC469805
0.7051	Intermediate Similarity	NPC311092
0.7051	Intermediate Similarity	NPC469799
0.7051	Intermediate Similarity	NPC469806
0.7051	Intermediate Similarity	NPC202389
0.7049	Intermediate Similarity	NPC244038
0.7049	Intermediate Similarity	NPC26906
0.7049	Intermediate Similarity	NPC214584
0.7031	Intermediate Similarity	NPC264779
0.7027	Intermediate Similarity	NPC471468
0.7027	Intermediate Similarity	NPC133580
0.7018	Intermediate Similarity	NPC192529
0.7015	Intermediate Similarity	NPC210346
0.7013	Intermediate Similarity	NPC469798
0.7013	Intermediate Similarity	NPC234193
0.7013	Intermediate Similarity	NPC241290
0.7013	Intermediate Similarity	NPC469797
0.7013	Intermediate Similarity	NPC164840
0.7013	Intermediate Similarity	NPC209944
0.7	Intermediate Similarity	NPC193770
0.7	Intermediate Similarity	NPC254886
0.7	Intermediate Similarity	NPC109528
0.7	Intermediate Similarity	NPC176107
0.7	Intermediate Similarity	NPC17810
0.6986	Remote Similarity	NPC474743
0.6986	Remote Similarity	NPC265485
0.6986	Remote Similarity	NPC68443
0.6986	Remote Similarity	NPC259049
0.6986	Remote Similarity	NPC153660
0.6986	Remote Similarity	NPC182717
0.6986	Remote Similarity	NPC471799
0.6986	Remote Similarity	NPC220939
0.6984	Remote Similarity	NPC5626
0.6974	Remote Similarity	NPC18603
0.6974	Remote Similarity	NPC307965
0.6974	Remote Similarity	NPC76931
0.697	Remote Similarity	NPC475716
0.6962	Remote Similarity	NPC3856
0.6962	Remote Similarity	NPC279639
0.6957	Remote Similarity	NPC268039
0.6944	Remote Similarity	NPC9161
0.6944	Remote Similarity	NPC49422
0.6944	Remote Similarity	NPC145498
0.6935	Remote Similarity	NPC40417
0.6935	Remote Similarity	NPC177112
0.6935	Remote Similarity	NPC71506
0.6935	Remote Similarity	NPC294358
0.6933	Remote Similarity	NPC106432
0.6933	Remote Similarity	NPC19907
0.6933	Remote Similarity	NPC292589
0.6933	Remote Similarity	NPC112680
0.6923	Remote Similarity	NPC47761
0.6923	Remote Similarity	NPC249423
0.6923	Remote Similarity	NPC476646
0.6901	Remote Similarity	NPC188292
0.6901	Remote Similarity	NPC471238
0.6901	Remote Similarity	NPC260474
0.6901	Remote Similarity	NPC476945
0.6897	Remote Similarity	NPC202189
0.6892	Remote Similarity	NPC471797
0.6892	Remote Similarity	NPC306727
0.6885	Remote Similarity	NPC26960
0.6885	Remote Similarity	NPC182102
0.6883	Remote Similarity	NPC47982
0.6883	Remote Similarity	NPC242767
0.6883	Remote Similarity	NPC233295
0.6883	Remote Similarity	NPC30986
0.6883	Remote Similarity	NPC81306
0.6883	Remote Similarity	NPC209430
0.6883	Remote Similarity	NPC84694
0.6883	Remote Similarity	NPC143182
0.6883	Remote Similarity	NPC109546
0.6883	Remote Similarity	NPC28862
0.6875	Remote Similarity	NPC470800
0.6875	Remote Similarity	NPC469770
0.6875	Remote Similarity	NPC87552
0.6875	Remote Similarity	NPC205845
0.6875	Remote Similarity	NPC470893
0.6867	Remote Similarity	NPC118011
0.6867	Remote Similarity	NPC36668
0.6866	Remote Similarity	NPC240506
0.6866	Remote Similarity	NPC66020
0.6866	Remote Similarity	NPC234264
0.6866	Remote Similarity	NPC47840
0.6866	Remote Similarity	NPC127582
0.6857	Remote Similarity	NPC323005
0.6849	Remote Similarity	NPC164022

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 NPC469728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	2066
0.2-0.3	4362
0.3-0.4	1889
0.4-0.5	480
0.5-0.6	131
0.6-0.7	50
0.7-0.8	8
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
0.8167	Intermediate Similarity	NPD4219	Approved
0.7538	Intermediate Similarity	NPD4193	Approved
0.7538	Intermediate Similarity	NPD4194	Approved
0.7538	Intermediate Similarity	NPD4191	Approved
0.7538	Intermediate Similarity	NPD4192	Approved
0.75	Intermediate Similarity	NPD8264	Approved
0.72	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4784	Approved
0.7123	Intermediate Similarity	NPD4785	Approved
0.7083	Intermediate Similarity	NPD4243	Approved
0.7013	Intermediate Similarity	NPD7332	Phase 2
0.7013	Intermediate Similarity	NPD7514	Phase 3
0.7	Intermediate Similarity	NPD8262	Approved
0.6944	Remote Similarity	NPD7143	Approved
0.6944	Remote Similarity	NPD7144	Approved
0.6892	Remote Similarity	NPD4687	Approved
0.6892	Remote Similarity	NPD4058	Approved
0.6849	Remote Similarity	NPD7150	Approved
0.6849	Remote Similarity	NPD7151	Approved
0.6849	Remote Similarity	NPD7152	Approved
0.6842	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6922	Approved
0.6806	Remote Similarity	NPD6923	Approved
0.68	Remote Similarity	NPD4190	Phase 3
0.68	Remote Similarity	NPD5275	Approved
0.6765	Remote Similarity	NPD368	Approved
0.6753	Remote Similarity	NPD7145	Approved
0.6709	Remote Similarity	NPD6902	Approved
0.6707	Remote Similarity	NPD4623	Approved
0.6707	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6932	Approved
0.6623	Remote Similarity	NPD6925	Approved
0.6623	Remote Similarity	NPD5776	Phase 2
0.6622	Remote Similarity	NPD5276	Approved
0.6582	Remote Similarity	NPD6930	Phase 2
0.6582	Remote Similarity	NPD6931	Approved
0.6579	Remote Similarity	NPD7339	Approved
0.6579	Remote Similarity	NPD6942	Approved
0.6575	Remote Similarity	NPD4137	Phase 3
0.6571	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6898	Phase 1
0.6494	Remote Similarity	NPD6933	Approved
0.6494	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4691	Approved
0.6486	Remote Similarity	NPD4747	Approved
0.6456	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD342	Phase 1
0.6341	Remote Similarity	NPD6695	Phase 3
0.6324	Remote Similarity	NPD287	Approved
0.6316	Remote Similarity	NPD4732	Discontinued
0.631	Remote Similarity	NPD5280	Approved
0.631	Remote Similarity	NPD4694	Approved
0.6265	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD6683	Phase 2
0.622	Remote Similarity	NPD4221	Approved
0.622	Remote Similarity	NPD4223	Phase 3
0.619	Remote Similarity	NPD6893	Approved
0.6173	Remote Similarity	NPD7509	Discontinued
0.6173	Remote Similarity	NPD7525	Registered
0.6145	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5284	Approved
0.6136	Remote Similarity	NPD5281	Approved
0.6118	Remote Similarity	NPD5690	Phase 2
0.6071	Remote Similarity	NPD4197	Approved
0.6053	Remote Similarity	NPD6939	Phase 2
0.6053	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7750	Discontinued
0.6047	Remote Similarity	NPD7524	Approved
0.6024	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD1696	Phase 3
0.5976	Remote Similarity	NPD4695	Discontinued
0.5965	Remote Similarity	NPD319	Phase 1
0.5955	Remote Similarity	NPD7637	Suspended
0.5934	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6049	Phase 2
0.593	Remote Similarity	NPD4688	Approved
0.593	Remote Similarity	NPD4138	Approved
0.593	Remote Similarity	NPD4690	Approved
0.593	Remote Similarity	NPD5279	Phase 3
0.593	Remote Similarity	NPD4689	Approved
0.593	Remote Similarity	NPD4693	Phase 3
0.593	Remote Similarity	NPD5205	Approved
0.5882	Remote Similarity	NPD3666	Approved
0.5882	Remote Similarity	NPD4786	Approved
0.5882	Remote Similarity	NPD3133	Approved
0.5882	Remote Similarity	NPD3665	Phase 1
0.5843	Remote Similarity	NPD5207	Approved
0.5843	Remote Similarity	NPD4096	Approved
0.5843	Remote Similarity	NPD7136	Phase 2
0.5814	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4518	Approved
0.5795	Remote Similarity	NPD4722	Approved
0.5795	Remote Similarity	NPD4723	Approved
0.5783	Remote Similarity	NPD4748	Discontinued
0.5783	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7087	Discontinued
0.5778	Remote Similarity	NPD5694	Approved
0.575	Remote Similarity	NPD8039	Approved
0.5747	Remote Similarity	NPD3618	Phase 1
0.5747	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD3617	Approved
0.573	Remote Similarity	NPD6051	Approved
0.573	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD5133	Approved
0.5714	Remote Similarity	NPD4692	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5698	Remote Similarity	NPD3668	Phase 3
0.5692	Remote Similarity	NPD4220	Pre-registration
0.5684	Remote Similarity	NPD6404	Discontinued
0.5682	Remote Similarity	NPD3573	Approved
0.5667	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5692	Phase 3
0.5604	Remote Similarity	NPD6079	Approved
0.5604	Remote Similarity	NPD6050	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