NPASS Compound

Structure

NPC176621 OpenBabel07101718202D 21 21 0 0 1 0 0 0 0 0999 V2000 -1.2247 1.2247 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 -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 2.5981 -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 4.3301 -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 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 15 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 16 2 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 19 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 15 18 1 0 0 0 0 17 16 1 6 0 0 0 18 20 1 6 0 0 0 19 21 1 0 0 0 0 20 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	344.164
LogP:	4.212
LogD:	3.993
LogS:	-4.33
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	4.482
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:	-4.538
MDCK Permeability:	2.0521614715107717e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.41
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.722
Plasma Protein Binding (PPB):	90.26697540283203%
Volume Distribution (VD):	1.551
Pgp-substrate:	12.544861793518066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.44
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.801
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.473

ADMET: Excretion

Clearance (CL):	2.515
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.401
Carcinogencity:	0.117
Eye Corrosion:	0.877
Eye Irritation:	0.948
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC176621

Natural Product ID:	NPC176621
*Common Name:**	Fuscol
IUPAC Name:	(3E,5E)-6-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-2-methylhepta-3,5-dien-2-ol
Synonyms:	Fuscol
Standard InCHIKey:	PGZCBHXBAUSEPY-VHSBKHBUSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-8-20(7)13-11-17(14-18(20)15(2)3)16(4)10-9-12-19(5,6)21/h8-10,12,17-18,21H,1-2,11,13-14H2,3-7H3/b12-9+,16-10+/t17-,18+,20-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)/C(=C/C=C/C(C)(C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476288
PubChem CID:	10891538
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
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[21865038]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22734800]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	8

Activity Type	# Activity
Cell Line	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	520.0	nM	PMID[508010]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	2.0	mm	PMID[508008]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	0.0	mm	PMID[508008]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	4.18	ug.mL-1	PMID[508008]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	27.3	%	PMID[508009]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.1	%	PMID[508011]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	46.0	%	PMID[508012]

☑ 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 NPC176621 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	149
0.1-0.2	2018
0.2-0.3	12879
0.3-0.4	15467
0.4-0.5	8060
0.5-0.6	3359
0.6-0.7	694
0.7-0.8	64
0.8-0.85	5
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	NPC469728
0.8475	Intermediate Similarity	NPC11130
0.8281	Intermediate Similarity	NPC279434
0.8	Intermediate Similarity	NPC55412
0.8	Intermediate Similarity	NPC249645
0.7931	Intermediate Similarity	NPC208638
0.791	Intermediate Similarity	NPC476431
0.7857	Intermediate Similarity	NPC124851
0.7812	Intermediate Similarity	NPC174956
0.7727	Intermediate Similarity	NPC259156
0.7727	Intermediate Similarity	NPC242945
0.7727	Intermediate Similarity	NPC250977
0.7656	Intermediate Similarity	NPC41160
0.7619	Intermediate Similarity	NPC309825
0.7612	Intermediate Similarity	NPC114651
0.7576	Intermediate Similarity	NPC107258
0.7571	Intermediate Similarity	NPC130665
0.7538	Intermediate Similarity	NPC283247
0.7538	Intermediate Similarity	NPC81615
0.7536	Intermediate Similarity	NPC34834
0.7465	Intermediate Similarity	NPC201048
0.7465	Intermediate Similarity	NPC476366
0.7463	Intermediate Similarity	NPC149680
0.7463	Intermediate Similarity	NPC255781
0.7419	Intermediate Similarity	NPC39068
0.7414	Intermediate Similarity	NPC22765
0.7414	Intermediate Similarity	NPC17518
0.7397	Intermediate Similarity	NPC91665
0.7385	Intermediate Similarity	NPC326645
0.7385	Intermediate Similarity	NPC317025
0.7385	Intermediate Similarity	NPC210346
0.7385	Intermediate Similarity	NPC317177
0.7385	Intermediate Similarity	NPC329416
0.7361	Intermediate Similarity	NPC69383
0.7361	Intermediate Similarity	NPC32832
0.7361	Intermediate Similarity	NPC313179
0.7361	Intermediate Similarity	NPC171148
0.7353	Intermediate Similarity	NPC69649
0.7353	Intermediate Similarity	NPC68703
0.7333	Intermediate Similarity	NPC68014
0.7313	Intermediate Similarity	NPC64123
0.7288	Intermediate Similarity	NPC26960
0.7288	Intermediate Similarity	NPC182102
0.7286	Intermediate Similarity	NPC189745
0.7286	Intermediate Similarity	NPC475728
0.726	Intermediate Similarity	NPC470749
0.726	Intermediate Similarity	NPC265588
0.7246	Intermediate Similarity	NPC32055
0.7246	Intermediate Similarity	NPC216460
0.7246	Intermediate Similarity	NPC94192
0.7206	Intermediate Similarity	NPC222366
0.7206	Intermediate Similarity	NPC286669
0.7206	Intermediate Similarity	NPC476039
0.7206	Intermediate Similarity	NPC476406
0.7188	Intermediate Similarity	NPC60772
0.7188	Intermediate Similarity	NPC181872
0.7188	Intermediate Similarity	NPC469769
0.7179	Intermediate Similarity	NPC238485
0.7179	Intermediate Similarity	NPC231310
0.7162	Intermediate Similarity	NPC91594
0.7162	Intermediate Similarity	NPC132542
0.7162	Intermediate Similarity	NPC470758
0.7162	Intermediate Similarity	NPC470711
0.7143	Intermediate Similarity	NPC469805
0.7143	Intermediate Similarity	NPC471560
0.7143	Intermediate Similarity	NPC474248
0.7143	Intermediate Similarity	NPC469804
0.7123	Intermediate Similarity	NPC476346
0.7121	Intermediate Similarity	NPC60565
0.7101	Intermediate Similarity	NPC171225
0.7101	Intermediate Similarity	NPC197805
0.7101	Intermediate Similarity	NPC254886
0.7083	Intermediate Similarity	NPC180015
0.7083	Intermediate Similarity	NPC109576
0.7083	Intermediate Similarity	NPC56747
0.7083	Intermediate Similarity	NPC474743
0.7083	Intermediate Similarity	NPC130016
0.7083	Intermediate Similarity	NPC68443
0.7067	Intermediate Similarity	NPC471409
0.7067	Intermediate Similarity	NPC83351
0.7067	Intermediate Similarity	NPC179028
0.7067	Intermediate Similarity	NPC275494
0.7067	Intermediate Similarity	NPC167891
0.7059	Intermediate Similarity	NPC308844
0.7059	Intermediate Similarity	NPC163678
0.7051	Intermediate Similarity	NPC3856
0.7051	Intermediate Similarity	NPC470384
0.7051	Intermediate Similarity	NPC279639
0.7049	Intermediate Similarity	NPC35519
0.7049	Intermediate Similarity	NPC179169
0.7049	Intermediate Similarity	NPC306195
0.7049	Intermediate Similarity	NPC157781
0.7049	Intermediate Similarity	NPC181255
0.7042	Intermediate Similarity	NPC9161
0.7042	Intermediate Similarity	NPC49422
0.7027	Intermediate Similarity	NPC244488
0.7027	Intermediate Similarity	NPC247325
0.7015	Intermediate Similarity	NPC474480
0.7013	Intermediate Similarity	NPC4166
0.7013	Intermediate Similarity	NPC264245
0.7	Intermediate Similarity	NPC471238
0.7	Intermediate Similarity	NPC329773
0.7	Intermediate Similarity	NPC96484
0.7	Intermediate Similarity	NPC208999
0.6986	Remote Similarity	NPC104644
0.6986	Remote Similarity	NPC306727
0.6984	Remote Similarity	NPC329686
0.6974	Remote Similarity	NPC233295
0.697	Remote Similarity	NPC240506
0.697	Remote Similarity	NPC234264
0.697	Remote Similarity	NPC47840
0.697	Remote Similarity	NPC323153
0.697	Remote Similarity	NPC471081
0.697	Remote Similarity	NPC135648
0.6964	Remote Similarity	NPC105246
0.6964	Remote Similarity	NPC190232
0.6957	Remote Similarity	NPC202017
0.6944	Remote Similarity	NPC470078
0.6944	Remote Similarity	NPC133253
0.6944	Remote Similarity	NPC167706
0.6944	Remote Similarity	NPC95863
0.6944	Remote Similarity	NPC471272
0.6923	Remote Similarity	NPC218616
0.6923	Remote Similarity	NPC49964
0.6923	Remote Similarity	NPC469799
0.6923	Remote Similarity	NPC87489
0.6923	Remote Similarity	NPC296701
0.6923	Remote Similarity	NPC469806
0.6923	Remote Similarity	NPC311092
0.6923	Remote Similarity	NPC202389
0.6912	Remote Similarity	NPC96793
0.6912	Remote Similarity	NPC469662
0.6912	Remote Similarity	NPC323424
0.6912	Remote Similarity	NPC107540
0.6912	Remote Similarity	NPC329698
0.6912	Remote Similarity	NPC225415
0.6912	Remote Similarity	NPC290367
0.6912	Remote Similarity	NPC475704
0.6901	Remote Similarity	NPC473893
0.6901	Remote Similarity	NPC269877
0.6901	Remote Similarity	NPC9942
0.6901	Remote Similarity	NPC167272
0.6897	Remote Similarity	NPC86683
0.6892	Remote Similarity	NPC471468
0.6892	Remote Similarity	NPC133580
0.6885	Remote Similarity	NPC214584
0.6885	Remote Similarity	NPC244038
0.6885	Remote Similarity	NPC26906
0.6883	Remote Similarity	NPC474592
0.6883	Remote Similarity	NPC469798
0.6883	Remote Similarity	NPC209944
0.6883	Remote Similarity	NPC234193
0.6883	Remote Similarity	NPC164840
0.6883	Remote Similarity	NPC469797
0.6883	Remote Similarity	NPC241290
0.6875	Remote Similarity	NPC264779
0.6875	Remote Similarity	NPC179024
0.6875	Remote Similarity	NPC473865
0.6875	Remote Similarity	NPC109528
0.6875	Remote Similarity	NPC474643
0.6866	Remote Similarity	NPC79576
0.6866	Remote Similarity	NPC194208
0.6866	Remote Similarity	NPC282694
0.6857	Remote Similarity	NPC176107
0.6857	Remote Similarity	NPC101307
0.6857	Remote Similarity	NPC88454
0.6857	Remote Similarity	NPC117607
0.6849	Remote Similarity	NPC153660
0.6849	Remote Similarity	NPC471799
0.6849	Remote Similarity	NPC182717
0.6842	Remote Similarity	NPC76931
0.6842	Remote Similarity	NPC297996
0.6842	Remote Similarity	NPC18603
0.6842	Remote Similarity	NPC11908
0.6842	Remote Similarity	NPC307965
0.6833	Remote Similarity	NPC17810
0.6825	Remote Similarity	NPC5626
0.6818	Remote Similarity	NPC5698
0.6818	Remote Similarity	NPC475931
0.6812	Remote Similarity	NPC268039
0.6812	Remote Similarity	NPC19569
0.6806	Remote Similarity	NPC145498
0.68	Remote Similarity	NPC106432
0.68	Remote Similarity	NPC253190
0.68	Remote Similarity	NPC112680
0.68	Remote Similarity	NPC292589
0.6795	Remote Similarity	NPC6663
0.6795	Remote Similarity	NPC249423
0.6795	Remote Similarity	NPC476646
0.6795	Remote Similarity	NPC47761
0.6774	Remote Similarity	NPC294358
0.6774	Remote Similarity	NPC71506
0.6774	Remote Similarity	NPC177112
0.6774	Remote Similarity	NPC40417
0.6765	Remote Similarity	NPC124112
0.6765	Remote Similarity	NPC202118
0.6765	Remote Similarity	NPC197238
0.6761	Remote Similarity	NPC310992
0.6761	Remote Similarity	NPC476945
0.6761	Remote Similarity	NPC160209

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 NPC176621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	2173
0.2-0.3	4352
0.3-0.4	1814
0.4-0.5	501
0.5-0.6	100
0.6-0.7	46
0.7-0.8	4
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
0.8	Intermediate Similarity	NPD4219	Approved
0.7385	Intermediate Similarity	NPD4194	Approved
0.7385	Intermediate Similarity	NPD4191	Approved
0.7385	Intermediate Similarity	NPD4193	Approved
0.7385	Intermediate Similarity	NPD4192	Approved
0.7361	Intermediate Similarity	NPD8264	Approved
0.7297	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7514	Phase 3
0.7105	Intermediate Similarity	NPD7332	Phase 2
0.7042	Intermediate Similarity	NPD7144	Approved
0.7042	Intermediate Similarity	NPD7143	Approved
0.6986	Remote Similarity	NPD4785	Approved
0.6986	Remote Similarity	NPD4784	Approved
0.6964	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4243	Approved
0.6944	Remote Similarity	NPD7150	Approved
0.6944	Remote Similarity	NPD7151	Approved
0.6944	Remote Similarity	NPD7152	Approved
0.6901	Remote Similarity	NPD6922	Approved
0.6901	Remote Similarity	NPD6923	Approved
0.6842	Remote Similarity	NPD7145	Approved
0.6833	Remote Similarity	NPD8262	Approved
0.6795	Remote Similarity	NPD6902	Approved
0.6757	Remote Similarity	NPD6926	Approved
0.6757	Remote Similarity	NPD6924	Approved
0.6711	Remote Similarity	NPD5776	Phase 2
0.6711	Remote Similarity	NPD6932	Approved
0.6711	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD368	Approved
0.6582	Remote Similarity	NPD6898	Phase 1
0.6579	Remote Similarity	NPD6933	Approved
0.6538	Remote Similarity	NPD6929	Approved
0.6533	Remote Similarity	NPD4687	Approved
0.6533	Remote Similarity	NPD4058	Approved
0.6533	Remote Similarity	NPD5733	Approved
0.6447	Remote Similarity	NPD4190	Phase 3
0.6447	Remote Similarity	NPD6942	Approved
0.6447	Remote Similarity	NPD5275	Approved
0.6447	Remote Similarity	NPD7339	Approved
0.642	Remote Similarity	NPD6695	Phase 3
0.64	Remote Similarity	NPD4732	Discontinued
0.6386	Remote Similarity	NPD4623	Approved
0.6386	Remote Similarity	NPD4519	Discontinued
0.6341	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4195	Approved
0.6329	Remote Similarity	NPD6683	Phase 2
0.6301	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5276	Approved
0.6265	Remote Similarity	NPD6893	Approved
0.625	Remote Similarity	NPD7525	Registered
0.625	Remote Similarity	NPD7509	Discontinued
0.6216	Remote Similarity	NPD4137	Phase 3
0.6212	Remote Similarity	NPD342	Phase 1
0.6176	Remote Similarity	NPD287	Approved
0.6154	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4747	Approved
0.6133	Remote Similarity	NPD4691	Approved
0.6125	Remote Similarity	NPD7645	Phase 2
0.6118	Remote Similarity	NPD7524	Approved
0.6118	Remote Similarity	NPD7750	Discontinued
0.6118	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6049	Phase 2
0.6	Remote Similarity	NPD4694	Approved
0.6	Remote Similarity	NPD5280	Approved
0.5921	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD6939	Phase 2
0.5909	Remote Similarity	NPD7136	Phase 2
0.5904	Remote Similarity	NPD4221	Approved
0.5904	Remote Similarity	NPD4223	Phase 3
0.5882	Remote Similarity	NPD1696	Phase 3
0.5882	Remote Similarity	NPD5329	Approved
0.5843	Remote Similarity	NPD5281	Approved
0.5843	Remote Similarity	NPD7087	Discontinued
0.5843	Remote Similarity	NPD5284	Approved
0.5833	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD8039	Approved
0.5814	Remote Similarity	NPD5690	Phase 2
0.5802	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD319	Phase 1
0.5781	Remote Similarity	NPD4220	Pre-registration
0.5765	Remote Similarity	NPD4197	Approved
0.5765	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD3667	Approved
0.5663	Remote Similarity	NPD4695	Discontinued
0.5663	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5205	Approved
0.5632	Remote Similarity	NPD4693	Phase 3
0.5632	Remote Similarity	NPD4138	Approved
0.5632	Remote Similarity	NPD4689	Approved
0.5632	Remote Similarity	NPD4688	Approved
0.5632	Remote Similarity	NPD5279	Phase 3
0.5632	Remote Similarity	NPD4690	Approved
0.5618	Remote Similarity	NPD6051	Approved
0.5618	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7331	Phase 2

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