NPASS Compound

Structure

CID317460 OpenBabel06191716142D 43 45 0 0 1 0 0 0 0 0999 V2000 9.8627 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9345 -0.6494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7450 -0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3765 -1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9967 -3.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9345 -0.6494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1306 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2646 -3.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3986 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5326 -3.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -3.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 0.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4345 0.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0540 0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3546 -1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9345 -1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2024 0.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9345 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0322 0.5862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0238 -2.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -1.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 2 0 0 0 0 3 21 2 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 10 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 26 2 0 0 0 0 20 25 1 0 0 0 0 20 27 1 0 0 0 0 22 29 1 0 0 0 0 22 33 1 6 0 0 0 23 35 2 0 0 0 0 23 40 1 0 0 0 0 24 36 2 0 0 0 0 24 41 1 0 0 0 0 25 37 1 6 0 0 0 26 31 1 0 0 0 0 27 33 1 1 0 0 0 27 34 1 0 0 0 0 28 38 2 0 0 0 0 28 42 1 0 0 0 0 29 30 1 0 0 0 0 29 42 1 1 0 0 0 30 34 1 6 0 0 0 30 39 1 0 0 0 0 31 40 1 6 0 0 0 31 43 1 0 0 0 0 32 34 1 1 0 0 0 32 41 1 0 0 0 0 32 43 1 0 0 0 0 33 7 1 1 0 0 0 34 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.33
Volume:	628.971
LogP:	4.837
LogD:	2.55
LogS:	-4.591
# Rotatable Bonds:	16
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.073
Synthetic Accessibility Score:	5.995
Fsp3:	0.618
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.886
MDCK Permeability:	4.120222001802176e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.704

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	87.81970977783203%
Volume Distribution (VD):	1.915
Pgp-substrate:	6.345552921295166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.275
CYP2C9-inhibitor:	0.566
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	2.753
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.564
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.59
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.949
Carcinogencity:	0.301
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC317460

Natural Product ID:	NPC317460
*Common Name:**	Casearupestrin B
IUPAC Name:	[(1R,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-diacetyloxy-5,10-dihydroxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-9-yl] (2Z,4E)-deca-2,4-dienoate
Synonyms:	casearupestrin B
Standard InCHIKey:	WGHDGSZCVSIZQE-WWRGVMLBSA-N
Standard InCHI:	InChI=1S/C34H48O9/c1-8-10-11-12-13-14-15-16-28(38)42-29-22(4)33(7,18-17-21(3)9-2)27-20-25(37)19-26-31(40-23(5)35)43-32(41-24(6)36)34(26,27)30(29)39/h9,13-16,19,22,25,27,29-32,37,39H,2-3,8,10-12,17-18,20H2,1,4-7H3/b14-13+,16-15-/t22-,25+,27+,29-,30+,31+,32+,33-,34-/m1/s1
SMILES:	CCCCCC=CC=CC(=O)OC1C(C(C2CC(C=C3C2(C1O)C(OC3OC(=O)C)OC(=O)C)O)(C)CCC(=C)C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774418
PubChem CID:	52951397
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO2718	Casearia rupestris	Species	Salicaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21381705]
NPO2718	Casearia rupestris	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21381705]
NPO2718	Casearia rupestris	Species	Salicaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	850.0	nM	PMID[560362]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	1300.0	nM	PMID[560362]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	280.0	nM	PMID[560362]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	800.0	nM	PMID[560362]

☑ 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 NPC317460 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	199
0.1-0.2	1172
0.2-0.3	3860
0.3-0.4	6537
0.4-0.5	13542
0.5-0.6	8994
0.6-0.7	5748
0.7-0.8	2459
0.8-0.85	104
0.85-0.9	53
0.9-0.95	17
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470025
1.0	High Similarity	NPC328074
1.0	High Similarity	NPC321272
0.9904	High Similarity	NPC470027
0.9903	High Similarity	NPC17791
0.9806	High Similarity	NPC316708
0.9712	High Similarity	NPC470026
0.9612	High Similarity	NPC470024
0.9515	High Similarity	NPC109376
0.9423	High Similarity	NPC224660
0.9417	High Similarity	NPC172867
0.9333	High Similarity	NPC40728
0.9333	High Similarity	NPC316974
0.9238	High Similarity	NPC217921
0.9238	High Similarity	NPC311223
0.9238	High Similarity	NPC128795
0.9238	High Similarity	NPC135015
0.9238	High Similarity	NPC48548
0.9143	High Similarity	NPC88013
0.9143	High Similarity	NPC125423
0.9065	High Similarity	NPC119550
0.9048	High Similarity	NPC218158
0.8952	High Similarity	NPC81567
0.8952	High Similarity	NPC264867
0.8952	High Similarity	NPC470321
0.8952	High Similarity	NPC201880
0.8952	High Similarity	NPC473207
0.8857	High Similarity	NPC7613
0.8857	High Similarity	NPC134270
0.8857	High Similarity	NPC127933
0.8857	High Similarity	NPC7644
0.8857	High Similarity	NPC475889
0.8796	High Similarity	NPC206618
0.8785	High Similarity	NPC184512
0.8762	High Similarity	NPC471363
0.8762	High Similarity	NPC238397
0.8761	High Similarity	NPC470914
0.8738	High Similarity	NPC98112
0.8716	High Similarity	NPC177047
0.8704	High Similarity	NPC38948
0.8692	High Similarity	NPC82251
0.8692	High Similarity	NPC252296
0.8649	High Similarity	NPC264153
0.8649	High Similarity	NPC473159
0.8641	High Similarity	NPC171598
0.8611	High Similarity	NPC472390
0.8598	High Similarity	NPC470768
0.8585	High Similarity	NPC11956
0.8571	High Similarity	NPC473204
0.8571	High Similarity	NPC473545
0.8571	High Similarity	NPC472187
0.8544	High Similarity	NPC472189
0.8544	High Similarity	NPC471362
0.8544	High Similarity	NPC471372
0.8534	High Similarity	NPC471082
0.8519	High Similarity	NPC470763
0.8519	High Similarity	NPC470767
0.8519	High Similarity	NPC239961
0.8509	High Similarity	NPC473617
0.8509	High Similarity	NPC473828
0.8505	High Similarity	NPC281378
0.8505	High Similarity	NPC23584
0.8491	Intermediate Similarity	NPC198992
0.8491	Intermediate Similarity	NPC472554
0.8476	Intermediate Similarity	NPC471366
0.8476	Intermediate Similarity	NPC476800
0.8476	Intermediate Similarity	NPC472186
0.8476	Intermediate Similarity	NPC318917
0.8448	Intermediate Similarity	NPC233500
0.8435	Intermediate Similarity	NPC219656
0.8421	Intermediate Similarity	NPC23046
0.8421	Intermediate Similarity	NPC473968
0.8411	Intermediate Similarity	NPC201191
0.8411	Intermediate Similarity	NPC470571
0.8411	Intermediate Similarity	NPC472815
0.8411	Intermediate Similarity	NPC150463
0.8411	Intermediate Similarity	NPC472552
0.8393	Intermediate Similarity	NPC473125
0.8381	Intermediate Similarity	NPC472188
0.8376	Intermediate Similarity	NPC196130
0.8364	Intermediate Similarity	NPC475263
0.8364	Intermediate Similarity	NPC50124
0.8362	Intermediate Similarity	NPC48692
0.8348	Intermediate Similarity	NPC470515
0.8333	Intermediate Similarity	NPC207637
0.8333	Intermediate Similarity	NPC474124
0.8333	Intermediate Similarity	NPC120009
0.8333	Intermediate Similarity	NPC474575
0.8319	Intermediate Similarity	NPC49413
0.8319	Intermediate Similarity	NPC40133
0.8319	Intermediate Similarity	NPC44298
0.8319	Intermediate Similarity	NPC473128
0.8319	Intermediate Similarity	NPC290608
0.8318	Intermediate Similarity	NPC280991
0.8305	Intermediate Similarity	NPC219804
0.8302	Intermediate Similarity	NPC474440
0.8291	Intermediate Similarity	NPC476204
0.8291	Intermediate Similarity	NPC170084
0.8288	Intermediate Similarity	NPC475586
0.8276	Intermediate Similarity	NPC470911
0.8276	Intermediate Similarity	NPC470517
0.8276	Intermediate Similarity	NPC470915
0.8276	Intermediate Similarity	NPC122971
0.8273	Intermediate Similarity	NPC122816
0.8273	Intermediate Similarity	NPC475074
0.8273	Intermediate Similarity	NPC473586
0.8273	Intermediate Similarity	NPC471205
0.8269	Intermediate Similarity	NPC469491
0.8261	Intermediate Similarity	NPC203862
0.8257	Intermediate Similarity	NPC473543
0.8246	Intermediate Similarity	NPC475163
0.8241	Intermediate Similarity	NPC476471
0.8241	Intermediate Similarity	NPC214277
0.8241	Intermediate Similarity	NPC475344
0.8241	Intermediate Similarity	NPC121423
0.823	Intermediate Similarity	NPC231797
0.8224	Intermediate Similarity	NPC324841
0.8224	Intermediate Similarity	NPC64348
0.8224	Intermediate Similarity	NPC477972
0.8224	Intermediate Similarity	NPC161527
0.8224	Intermediate Similarity	NPC38855
0.8224	Intermediate Similarity	NPC219285
0.8224	Intermediate Similarity	NPC228251
0.8224	Intermediate Similarity	NPC477971
0.8224	Intermediate Similarity	NPC20113
0.8224	Intermediate Similarity	NPC477968
0.8214	Intermediate Similarity	NPC235014
0.8208	Intermediate Similarity	NPC91197
0.8208	Intermediate Similarity	NPC125551
0.8208	Intermediate Similarity	NPC96597
0.8208	Intermediate Similarity	NPC239547
0.8208	Intermediate Similarity	NPC309503
0.8208	Intermediate Similarity	NPC120446
0.8208	Intermediate Similarity	NPC155319
0.8205	Intermediate Similarity	NPC135369
0.8198	Intermediate Similarity	NPC181994
0.819	Intermediate Similarity	NPC234522
0.819	Intermediate Similarity	NPC275310
0.819	Intermediate Similarity	NPC230347
0.819	Intermediate Similarity	NPC286612
0.8182	Intermediate Similarity	NPC470056
0.8182	Intermediate Similarity	NPC51719
0.8182	Intermediate Similarity	NPC88349
0.8182	Intermediate Similarity	NPC470055
0.8174	Intermediate Similarity	NPC471816
0.8167	Intermediate Similarity	NPC179261
0.8165	Intermediate Similarity	NPC473523
0.8165	Intermediate Similarity	NPC45897
0.8165	Intermediate Similarity	NPC473070
0.8158	Intermediate Similarity	NPC474410
0.8158	Intermediate Similarity	NPC469496
0.8158	Intermediate Similarity	NPC469463
0.8158	Intermediate Similarity	NPC469454
0.8158	Intermediate Similarity	NPC287075
0.8158	Intermediate Similarity	NPC293658
0.8155	Intermediate Similarity	NPC469403
0.8155	Intermediate Similarity	NPC470817
0.8151	Intermediate Similarity	NPC41129
0.8148	Intermediate Similarity	NPC475617
0.8142	Intermediate Similarity	NPC208189
0.8142	Intermediate Similarity	NPC65034
0.8136	Intermediate Similarity	NPC202051
0.8131	Intermediate Similarity	NPC477928
0.8131	Intermediate Similarity	NPC473154
0.8125	Intermediate Similarity	NPC257853
0.812	Intermediate Similarity	NPC44899
0.812	Intermediate Similarity	NPC475775
0.812	Intermediate Similarity	NPC29639
0.812	Intermediate Similarity	NPC304260
0.812	Intermediate Similarity	NPC5883
0.812	Intermediate Similarity	NPC268326
0.812	Intermediate Similarity	NPC153085
0.812	Intermediate Similarity	NPC476529
0.8115	Intermediate Similarity	NPC476966
0.8115	Intermediate Similarity	NPC471407
0.8113	Intermediate Similarity	NPC284194
0.8113	Intermediate Similarity	NPC165632
0.8113	Intermediate Similarity	NPC221801
0.8113	Intermediate Similarity	NPC211810
0.8113	Intermediate Similarity	NPC471765
0.8113	Intermediate Similarity	NPC473153
0.8108	Intermediate Similarity	NPC293512
0.8108	Intermediate Similarity	NPC33053
0.8103	Intermediate Similarity	NPC93883
0.8103	Intermediate Similarity	NPC474483
0.8103	Intermediate Similarity	NPC152615
0.8095	Intermediate Similarity	NPC256368
0.8095	Intermediate Similarity	NPC88507
0.8095	Intermediate Similarity	NPC472360
0.8095	Intermediate Similarity	NPC470255
0.8095	Intermediate Similarity	NPC472416
0.8091	Intermediate Similarity	NPC85593
0.8091	Intermediate Similarity	NPC75608
0.8091	Intermediate Similarity	NPC93352
0.8091	Intermediate Similarity	NPC473068
0.8091	Intermediate Similarity	NPC194941
0.8091	Intermediate Similarity	NPC31430
0.8087	Intermediate Similarity	NPC181145
0.8083	Intermediate Similarity	NPC469379
0.8083	Intermediate Similarity	NPC471090

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 NPC317460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1356
0.2-0.3	3618
0.3-0.4	2584
0.4-0.5	918
0.5-0.6	323
0.6-0.7	153
0.7-0.8	25
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
0.8291	Intermediate Similarity	NPD7503	Approved
0.8036	Intermediate Similarity	NPD6686	Approved
0.7983	Intermediate Similarity	NPD8033	Approved
0.7966	Intermediate Similarity	NPD7516	Approved
0.7899	Intermediate Similarity	NPD8377	Approved
0.7899	Intermediate Similarity	NPD8294	Approved
0.7881	Intermediate Similarity	NPD7327	Approved
0.7881	Intermediate Similarity	NPD7328	Approved
0.7833	Intermediate Similarity	NPD8378	Approved
0.7833	Intermediate Similarity	NPD8296	Approved
0.7833	Intermediate Similarity	NPD8335	Approved
0.7833	Intermediate Similarity	NPD8379	Approved
0.7833	Intermediate Similarity	NPD8380	Approved
0.7818	Intermediate Similarity	NPD5344	Discontinued
0.7798	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD6648	Approved
0.7686	Intermediate Similarity	NPD8516	Approved
0.7686	Intermediate Similarity	NPD8515	Approved
0.7686	Intermediate Similarity	NPD8513	Phase 3
0.7686	Intermediate Similarity	NPD8517	Approved
0.7642	Intermediate Similarity	NPD7838	Discovery
0.7636	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7507	Approved
0.7411	Intermediate Similarity	NPD7639	Approved
0.7411	Intermediate Similarity	NPD7640	Approved
0.735	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7638	Approved
0.7266	Intermediate Similarity	NPD7319	Approved
0.7238	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7115	Discovery
0.7203	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7736	Approved
0.7179	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7109	Intermediate Similarity	NPD8074	Phase 3
0.7107	Intermediate Similarity	NPD8133	Approved
0.7063	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8293	Discontinued
0.6953	Remote Similarity	NPD7492	Approved
0.6942	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6054	Approved
0.6899	Remote Similarity	NPD6616	Approved
0.6885	Remote Similarity	NPD8297	Approved
0.6885	Remote Similarity	NPD6882	Approved
0.6881	Remote Similarity	NPD7524	Approved
0.6847	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6698	Approved
0.6846	Remote Similarity	NPD7078	Approved
0.6838	Remote Similarity	NPD7632	Discontinued
0.68	Remote Similarity	NPD6009	Approved
0.6786	Remote Similarity	NPD7637	Suspended
0.6786	Remote Similarity	NPD7983	Approved
0.6772	Remote Similarity	NPD6319	Approved
0.675	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5778	Approved
0.6726	Remote Similarity	NPD5779	Approved
0.6719	Remote Similarity	NPD6015	Approved
0.6719	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6641	Remote Similarity	NPD6059	Approved
0.6615	Remote Similarity	NPD6067	Discontinued
0.6615	Remote Similarity	NPD7830	Approved
0.6615	Remote Similarity	NPD7829	Approved
0.6612	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6371	Approved
0.6557	Remote Similarity	NPD6881	Approved
0.6557	Remote Similarity	NPD6899	Approved
0.6557	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD8264	Approved
0.6532	Remote Similarity	NPD8130	Phase 1
0.6532	Remote Similarity	NPD6650	Approved
0.6532	Remote Similarity	NPD6649	Approved
0.6522	Remote Similarity	NPD7748	Approved
0.6519	Remote Similarity	NPD7260	Phase 2
0.6514	Remote Similarity	NPD6695	Phase 3
0.6496	Remote Similarity	NPD7902	Approved
0.6475	Remote Similarity	NPD5697	Approved
0.6458	Remote Similarity	NPD7625	Phase 1
0.6452	Remote Similarity	NPD7290	Approved
0.6452	Remote Similarity	NPD6883	Approved
0.6452	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD7750	Discontinued
0.6403	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6847	Approved
0.64	Remote Similarity	NPD6869	Approved
0.64	Remote Similarity	NPD6617	Approved
0.6393	Remote Similarity	NPD6402	Approved
0.6393	Remote Similarity	NPD5739	Approved
0.6393	Remote Similarity	NPD6675	Approved
0.6393	Remote Similarity	NPD7128	Approved
0.6371	Remote Similarity	NPD6014	Approved
0.6371	Remote Similarity	NPD6012	Approved
0.6371	Remote Similarity	NPD6372	Approved
0.6371	Remote Similarity	NPD6373	Approved
0.6371	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD7604	Phase 2
0.6349	Remote Similarity	NPD6053	Discontinued
0.6348	Remote Similarity	NPD6411	Approved
0.6348	Remote Similarity	NPD7515	Phase 2
0.6336	Remote Similarity	NPD5983	Phase 2
0.6296	Remote Similarity	NPD6929	Approved
0.6293	Remote Similarity	NPD6399	Phase 3
0.629	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD7320	Approved
0.6281	Remote Similarity	NPD5211	Phase 2
0.6273	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7839	Suspended
0.6269	Remote Similarity	NPD6336	Discontinued
0.6269	Remote Similarity	NPD8451	Approved
0.626	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD7266	Discontinued
0.625	Remote Similarity	NPD7799	Discontinued
0.6239	Remote Similarity	NPD7900	Approved
0.6239	Remote Similarity	NPD7332	Phase 2
0.6239	Remote Similarity	NPD6931	Approved
0.6239	Remote Similarity	NPD6930	Phase 2
0.6239	Remote Similarity	NPD7514	Phase 3
0.6239	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6845	Suspended
0.6231	Remote Similarity	NPD7641	Discontinued
0.6222	Remote Similarity	NPD8448	Approved
0.6212	Remote Similarity	NPD8444	Approved
0.6211	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5701	Approved
0.6207	Remote Similarity	NPD6079	Approved
0.6204	Remote Similarity	NPD7145	Approved
0.6194	Remote Similarity	NPD8299	Approved
0.6194	Remote Similarity	NPD8342	Approved
0.6194	Remote Similarity	NPD8340	Approved
0.6194	Remote Similarity	NPD8341	Approved
0.619	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4634	Approved
0.6186	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6902	Approved
0.6179	Remote Similarity	NPD5141	Approved
0.6176	Remote Similarity	NPD6033	Approved
0.6174	Remote Similarity	NPD6101	Approved
0.6174	Remote Similarity	NPD6051	Approved
0.6174	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD5126	Approved
0.6165	Remote Similarity	NPD5125	Phase 3
0.6154	Remote Similarity	NPD8171	Discontinued
0.6147	Remote Similarity	NPD7645	Phase 2
0.614	Remote Similarity	NPD4250	Approved
0.614	Remote Similarity	NPD4251	Approved
0.6129	Remote Similarity	NPD6640	Phase 3
0.6121	Remote Similarity	NPD5785	Approved
0.6121	Remote Similarity	NPD3168	Discontinued
0.6116	Remote Similarity	NPD4696	Approved
0.6116	Remote Similarity	NPD5285	Approved
0.6116	Remote Similarity	NPD5286	Approved
0.6115	Remote Similarity	NPD8449	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6111	Remote Similarity	NPD6925	Approved
0.6091	Remote Similarity	NPD7525	Registered
0.609	Remote Similarity	NPD6921	Approved
0.6087	Remote Similarity	NPD8391	Approved
0.6087	Remote Similarity	NPD8392	Approved
0.6087	Remote Similarity	NPD8390	Approved
0.6083	Remote Similarity	NPD6084	Phase 2
0.6083	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD8450	Suspended
0.6068	Remote Similarity	NPD7087	Discontinued
0.6066	Remote Similarity	NPD4159	Approved
0.6061	Remote Similarity	NPD7100	Approved
0.6061	Remote Similarity	NPD7101	Approved
0.6053	Remote Similarity	NPD3618	Phase 1
0.6053	Remote Similarity	NPD4249	Approved
0.6034	Remote Similarity	NPD5328	Approved
0.6031	Remote Similarity	NPD7505	Discontinued
0.6019	Remote Similarity	NPD6933	Approved
0.6016	Remote Similarity	NPD5225	Approved
0.6016	Remote Similarity	NPD4633	Approved
0.6016	Remote Similarity	NPD5226	Approved
0.6016	Remote Similarity	NPD5224	Approved
0.6016	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD8338	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5988	Remote Similarity	NPD8407	Phase 2
0.5985	Remote Similarity	NPD6335	Approved
0.5971	Remote Similarity	NPD5956	Approved
0.5968	Remote Similarity	NPD5174	Approved
0.5968	Remote Similarity	NPD5175	Approved
0.5965	Remote Similarity	NPD1696	Phase 3
0.5965	Remote Similarity	NPD6893	Approved
0.5963	Remote Similarity	NPD6932	Approved
0.5957	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD6868	Approved
0.5954	Remote Similarity	NPD6274	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