NPASS Compound

Structure

NPC471081 OpenBabel07101718312D 21 22 0 0 1 0 0 0 0 0999 V2000 -2.4627 -2.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8737 -2.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5551 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0350 1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -2.3843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3632 -1.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 1.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 -0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6182 0.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 0.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0426 -1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2251 0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4692 -2.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 -2.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5350 0.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4143 -0.8283 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0712 -1.2127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 0 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 4.4098 -0.9234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 17 21 1 6 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.091
LogD:	4.474
LogS:	-4.801
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	4.581
Fsp3:	0.7
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:	-4.659
MDCK Permeability:	2.5786630430957302e-05
Pgp-inhibitor:	0.74
Pgp-substrate:	0.879
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.586
Plasma Protein Binding (PPB):	95.97295379638672%
Volume Distribution (VD):	1.461
Pgp-substrate:	1.7755987644195557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.926
CYP2C9-inhibitor:	0.3
CYP2C9-substrate:	0.425
CYP2D6-inhibitor:	0.523
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	9.584
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.201
Carcinogencity:	0.108
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.424

Download Data

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

Natural Product: NPC471081

Natural Product ID:	NPC471081
*Common Name:**	Dolabellatrienol
IUPAC Name:	(3aS,5E,8S,9E)-3a,6,10-trimethyl-1-propan-2-yl-3,4,7,8,11,12-hexahydro-2H-cyclopenta[11]annulen-8-ol
Synonyms:	Dolabellatrienol
Standard InCHIKey:	JMABOHOFIQCYCW-YSNVBICFSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14(2)18-9-11-20(5)10-8-16(4)13-17(21)12-15(3)6-7-19(18)20/h8,12,14,17,21H,6-7,9-11,13H2,1-5H3/b15-12+,16-8+/t17-,20-/m1/s1
SMILES:	C/C/1=C[C@@H](O)C/C(=C/C[C@]2(C(=C(CC2)C(C)C)CC1)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2367498
PubChem CID:	53321983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO32968	dictoyota dichotoma	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21130542]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	102.3	ug.mL-1	PMID[460139]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	120.6	ug.mL-1	PMID[460139]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	150.5	ug.mL-1	PMID[460139]
NPT27	Others	Unspecified		IC50	=	100.6	ug.mL-1	PMID[460139]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	15.1	%	PMID[460139]
NPT632	Tissue	Brain	Rattus norvegicus	Inhibition	=	24.36	%	PMID[460139]
NPT27	Others	Unspecified		Activity	=	5.75	%	PMID[460139]

☑ 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 NPC471081 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	143
0.1-0.2	2334
0.2-0.3	13953
0.3-0.4	13927
0.4-0.5	7536
0.5-0.6	3847
0.6-0.7	802
0.7-0.8	132
0.8-0.85	18
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC19569
0.85	High Similarity	NPC122239
0.8448	Intermediate Similarity	NPC298299
0.8448	Intermediate Similarity	NPC329686
0.8254	Intermediate Similarity	NPC309300
0.8226	Intermediate Similarity	NPC274704
0.8226	Intermediate Similarity	NPC210346
0.8214	Intermediate Similarity	NPC182102
0.8214	Intermediate Similarity	NPC26960
0.8154	Intermediate Similarity	NPC477791
0.8154	Intermediate Similarity	NPC114651
0.8095	Intermediate Similarity	NPC279200
0.8033	Intermediate Similarity	NPC226848
0.8033	Intermediate Similarity	NPC181872
0.803	Intermediate Similarity	NPC224532
0.7969	Intermediate Similarity	NPC110241
0.7941	Intermediate Similarity	NPC471662
0.7931	Intermediate Similarity	NPC35756
0.791	Intermediate Similarity	NPC217570
0.791	Intermediate Similarity	NPC90115
0.7903	Intermediate Similarity	NPC475931
0.7869	Intermediate Similarity	NPC11130
0.7846	Intermediate Similarity	NPC187619
0.7846	Intermediate Similarity	NPC238352
0.7846	Intermediate Similarity	NPC477009
0.7812	Intermediate Similarity	NPC473759
0.7812	Intermediate Similarity	NPC474155
0.7794	Intermediate Similarity	NPC189745
0.7778	Intermediate Similarity	NPC234264
0.7778	Intermediate Similarity	NPC47840
0.7761	Intermediate Similarity	NPC167527
0.7759	Intermediate Similarity	NPC474495
0.7759	Intermediate Similarity	NPC473672
0.7742	Intermediate Similarity	NPC475830
0.7742	Intermediate Similarity	NPC155025
0.7727	Intermediate Similarity	NPC272125
0.7727	Intermediate Similarity	NPC162309
0.7705	Intermediate Similarity	NPC48891
0.7705	Intermediate Similarity	NPC473865
0.7705	Intermediate Similarity	NPC474643
0.7692	Intermediate Similarity	NPC290367
0.7647	Intermediate Similarity	NPC167272
0.7647	Intermediate Similarity	NPC269877
0.7619	Intermediate Similarity	NPC309825
0.7612	Intermediate Similarity	NPC472255
0.7612	Intermediate Similarity	NPC472253
0.7612	Intermediate Similarity	NPC136813
0.7606	Intermediate Similarity	NPC60818
0.7606	Intermediate Similarity	NPC23231
0.7576	Intermediate Similarity	NPC308844
0.7571	Intermediate Similarity	NPC474743
0.7541	Intermediate Similarity	NPC232247
0.7541	Intermediate Similarity	NPC251666
0.7541	Intermediate Similarity	NPC474644
0.7538	Intermediate Similarity	NPC473508
0.7538	Intermediate Similarity	NPC133368
0.7538	Intermediate Similarity	NPC124112
0.7538	Intermediate Similarity	NPC211291
0.7538	Intermediate Similarity	NPC474480
0.7536	Intermediate Similarity	NPC9161
0.7536	Intermediate Similarity	NPC286154
0.7536	Intermediate Similarity	NPC49422
0.7536	Intermediate Similarity	NPC34834
0.75	Intermediate Similarity	NPC310643
0.75	Intermediate Similarity	NPC305698
0.75	Intermediate Similarity	NPC99487
0.75	Intermediate Similarity	NPC247325
0.75	Intermediate Similarity	NPC244488
0.7465	Intermediate Similarity	NPC471659
0.7463	Intermediate Similarity	NPC250977
0.7458	Intermediate Similarity	NPC244038
0.7432	Intermediate Similarity	NPC143182
0.7432	Intermediate Similarity	NPC81306
0.7432	Intermediate Similarity	NPC84694
0.7432	Intermediate Similarity	NPC28862
0.7432	Intermediate Similarity	NPC47982
0.7432	Intermediate Similarity	NPC109546
0.7429	Intermediate Similarity	NPC474884
0.7424	Intermediate Similarity	NPC323424
0.7424	Intermediate Similarity	NPC96793
0.7424	Intermediate Similarity	NPC225415
0.7424	Intermediate Similarity	NPC475704
0.7419	Intermediate Similarity	NPC249645
0.7419	Intermediate Similarity	NPC55412
0.7391	Intermediate Similarity	NPC471560
0.7385	Intermediate Similarity	NPC475251
0.7361	Intermediate Similarity	NPC69383
0.7361	Intermediate Similarity	NPC313179
0.7361	Intermediate Similarity	NPC474011
0.7361	Intermediate Similarity	NPC171148
0.7353	Intermediate Similarity	NPC69649
0.7353	Intermediate Similarity	NPC68703
0.7353	Intermediate Similarity	NPC259299
0.7353	Intermediate Similarity	NPC73603
0.7344	Intermediate Similarity	NPC5698
0.7333	Intermediate Similarity	NPC234193
0.7324	Intermediate Similarity	NPC329763
0.7324	Intermediate Similarity	NPC234527
0.7324	Intermediate Similarity	NPC14352
0.7297	Intermediate Similarity	NPC474216
0.7288	Intermediate Similarity	NPC474460
0.7286	Intermediate Similarity	NPC4299
0.7286	Intermediate Similarity	NPC470041
0.7246	Intermediate Similarity	NPC208999
0.7246	Intermediate Similarity	NPC96484
0.7237	Intermediate Similarity	NPC264245
0.7237	Intermediate Similarity	NPC209620
0.7237	Intermediate Similarity	NPC23852
0.7231	Intermediate Similarity	NPC323153
0.7231	Intermediate Similarity	NPC240506
0.7231	Intermediate Similarity	NPC252809
0.7222	Intermediate Similarity	NPC306727
0.7222	Intermediate Similarity	NPC469593
0.7222	Intermediate Similarity	NPC329090
0.7222	Intermediate Similarity	NPC27395
0.7222	Intermediate Similarity	NPC469534
0.7222	Intermediate Similarity	NPC469533
0.7213	Intermediate Similarity	NPC474496
0.7206	Intermediate Similarity	NPC202017
0.7206	Intermediate Similarity	NPC311736
0.7206	Intermediate Similarity	NPC135650
0.7206	Intermediate Similarity	NPC326310
0.7206	Intermediate Similarity	NPC267027
0.72	Intermediate Similarity	NPC30986
0.72	Intermediate Similarity	NPC209430
0.7188	Intermediate Similarity	NPC10017
0.7183	Intermediate Similarity	NPC477792
0.7183	Intermediate Similarity	NPC472254
0.7164	Intermediate Similarity	NPC300593
0.7162	Intermediate Similarity	NPC91594
0.7162	Intermediate Similarity	NPC31037
0.7162	Intermediate Similarity	NPC262747
0.7143	Intermediate Similarity	NPC101462
0.7143	Intermediate Similarity	NPC469677
0.7143	Intermediate Similarity	NPC474248
0.7143	Intermediate Similarity	NPC473893
0.7143	Intermediate Similarity	NPC189972
0.7143	Intermediate Similarity	NPC472465
0.7143	Intermediate Similarity	NPC101622
0.7143	Intermediate Similarity	NPC329989
0.7143	Intermediate Similarity	NPC50964
0.7143	Intermediate Similarity	NPC239373
0.7143	Intermediate Similarity	NPC49964
0.7123	Intermediate Similarity	NPC319090
0.7123	Intermediate Similarity	NPC288035
0.7123	Intermediate Similarity	NPC162742
0.7123	Intermediate Similarity	NPC313185
0.7123	Intermediate Similarity	NPC474885
0.7123	Intermediate Similarity	NPC28657
0.7123	Intermediate Similarity	NPC22105
0.7123	Intermediate Similarity	NPC134847
0.7123	Intermediate Similarity	NPC285893
0.7123	Intermediate Similarity	NPC328104
0.7123	Intermediate Similarity	NPC136188
0.7123	Intermediate Similarity	NPC230301
0.7123	Intermediate Similarity	NPC304309
0.7121	Intermediate Similarity	NPC207007
0.7121	Intermediate Similarity	NPC321867
0.7121	Intermediate Similarity	NPC68679
0.7121	Intermediate Similarity	NPC260573
0.7121	Intermediate Similarity	NPC225342
0.7105	Intermediate Similarity	NPC241290
0.7105	Intermediate Similarity	NPC324772
0.7105	Intermediate Similarity	NPC209944
0.7105	Intermediate Similarity	NPC164840
0.7101	Intermediate Similarity	NPC45782
0.7101	Intermediate Similarity	NPC163290
0.7083	Intermediate Similarity	NPC130665
0.7083	Intermediate Similarity	NPC474140
0.7067	Intermediate Similarity	NPC209135
0.7067	Intermediate Similarity	NPC474816
0.7067	Intermediate Similarity	NPC476314
0.7067	Intermediate Similarity	NPC83351
0.7067	Intermediate Similarity	NPC11908
0.7067	Intermediate Similarity	NPC473943
0.7067	Intermediate Similarity	NPC167891
0.7051	Intermediate Similarity	NPC474634
0.7051	Intermediate Similarity	NPC317458
0.7051	Intermediate Similarity	NPC470384
0.7051	Intermediate Similarity	NPC475789
0.7049	Intermediate Similarity	NPC68014
0.7042	Intermediate Similarity	NPC254845
0.7042	Intermediate Similarity	NPC145498
0.7027	Intermediate Similarity	NPC265588
0.7027	Intermediate Similarity	NPC315261
0.7027	Intermediate Similarity	NPC321016
0.7027	Intermediate Similarity	NPC113733
0.7027	Intermediate Similarity	NPC240604
0.7027	Intermediate Similarity	NPC321381
0.7027	Intermediate Similarity	NPC469646
0.7027	Intermediate Similarity	NPC300324
0.7027	Intermediate Similarity	NPC126969
0.7027	Intermediate Similarity	NPC471658
0.7027	Intermediate Similarity	NPC107059
0.7015	Intermediate Similarity	NPC83200
0.7013	Intermediate Similarity	NPC7505
0.7013	Intermediate Similarity	NPC474683
0.7013	Intermediate Similarity	NPC474731
0.7013	Intermediate Similarity	NPC82986
0.7013	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 NPC471081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	2815
0.2-0.3	4233
0.3-0.4	1473
0.4-0.5	344
0.5-0.6	84
0.6-0.7	45
0.7-0.8	6
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
0.7778	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6923	Approved
0.7647	Intermediate Similarity	NPD6922	Approved
0.7568	Intermediate Similarity	NPD7332	Phase 2
0.7536	Intermediate Similarity	NPD7144	Approved
0.7536	Intermediate Similarity	NPD7143	Approved
0.7429	Intermediate Similarity	NPD7151	Approved
0.7429	Intermediate Similarity	NPD7152	Approved
0.7429	Intermediate Similarity	NPD7150	Approved
0.7419	Intermediate Similarity	NPD4219	Approved
0.7397	Intermediate Similarity	NPD5776	Phase 2
0.7397	Intermediate Similarity	NPD6925	Approved
0.7361	Intermediate Similarity	NPD8264	Approved
0.7333	Intermediate Similarity	NPD7514	Phase 3
0.7297	Intermediate Similarity	NPD7145	Approved
0.7237	Intermediate Similarity	NPD6898	Phase 1
0.7237	Intermediate Similarity	NPD6902	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.72	Intermediate Similarity	NPD6929	Approved
0.7123	Intermediate Similarity	NPD6942	Approved
0.7123	Intermediate Similarity	NPD7339	Approved
0.7121	Intermediate Similarity	NPD368	Approved
0.7105	Intermediate Similarity	NPD6931	Approved
0.7105	Intermediate Similarity	NPD6930	Phase 2
0.7067	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6933	Approved
0.6984	Remote Similarity	NPD342	Phase 1
0.6933	Remote Similarity	NPD6932	Approved
0.6897	Remote Similarity	NPD4265	Approved
0.6883	Remote Similarity	NPD7509	Discontinued
0.6835	Remote Similarity	NPD5362	Discontinued
0.6835	Remote Similarity	NPD6695	Phase 3
0.6835	Remote Similarity	NPD7154	Phase 3
0.68	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6683	Phase 2
0.675	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6625	Remote Similarity	NPD5332	Approved
0.6625	Remote Similarity	NPD5331	Approved
0.6623	Remote Similarity	NPD4268	Approved
0.6623	Remote Similarity	NPD4271	Approved
0.6622	Remote Similarity	NPD4732	Discontinued
0.6582	Remote Similarity	NPD4790	Discontinued
0.6543	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7524	Approved
0.6506	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7750	Discontinued
0.65	Remote Similarity	NPD4269	Approved
0.65	Remote Similarity	NPD4270	Approved
0.6471	Remote Similarity	NPD7136	Phase 2
0.6456	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4252	Approved
0.6456	Remote Similarity	NPD7525	Registered
0.6395	Remote Similarity	NPD7637	Suspended
0.6341	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD4785	Approved
0.6316	Remote Similarity	NPD4784	Approved
0.6296	Remote Similarity	NPD3667	Approved
0.6279	Remote Similarity	NPD5785	Approved
0.6267	Remote Similarity	NPD4243	Approved
0.6265	Remote Similarity	NPD5363	Approved
0.6207	Remote Similarity	NPD7087	Discontinued
0.619	Remote Similarity	NPD5786	Approved
0.6143	Remote Similarity	NPD4191	Approved
0.6143	Remote Similarity	NPD4194	Approved
0.6143	Remote Similarity	NPD4192	Approved
0.6143	Remote Similarity	NPD4193	Approved
0.6125	Remote Similarity	NPD7645	Phase 2
0.6071	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD5369	Approved
0.5972	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3666	Approved
0.5952	Remote Similarity	NPD3133	Approved
0.5952	Remote Similarity	NPD3665	Phase 1
0.593	Remote Similarity	NPD4250	Approved
0.593	Remote Similarity	NPD4251	Approved
0.589	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1696	Phase 3
0.5854	Remote Similarity	NPD4748	Discontinued
0.5854	Remote Similarity	NPD5368	Approved
0.5823	Remote Similarity	NPD4190	Phase 3
0.5823	Remote Similarity	NPD5275	Approved
0.5814	Remote Similarity	NPD4249	Approved
0.5814	Remote Similarity	NPD3618	Phase 1
0.5814	Remote Similarity	NPD5279	Phase 3
0.5795	Remote Similarity	NPD5328	Approved
0.5773	Remote Similarity	NPD6640	Phase 3
0.5765	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD7640	Approved
0.5745	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD6435	Approved
0.5667	Remote Similarity	NPD6079	Approved
0.5667	Remote Similarity	NPD7983	Approved
0.5638	Remote Similarity	NPD4225	Approved
0.5638	Remote Similarity	NPD7638	Approved
0.5632	Remote Similarity	NPD4519	Discontinued
0.5632	Remote Similarity	NPD4623	Approved
0.5618	Remote Similarity	NPD5370	Suspended
0.5604	Remote Similarity	NPD6399	Phase 3
0.5604	Remote Similarity	NPD5778	Approved
0.5604	Remote Similarity	NPD5779	Approved
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