NPASS Compound

Structure

CID96377 OpenBabel06191715432D 36 40 0 0 1 0 0 0 0 0999 V2000 3.7012 2.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6496 1.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0978 -0.8946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4359 -1.6431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6682 -1.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3986 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5488 0.4903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8492 1.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3980 -2.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8498 -1.4719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5485 -2.4530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2481 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8492 -0.4903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9053 1.4205 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8009 1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6988 0.0008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5401 -2.0420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3986 -0.9816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2478 -2.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6990 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8498 0.4906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6990 -0.9816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8492 0.4903 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2747 0.7940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2496 0.6918 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6987 0.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5488 -1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4376 -3.0172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1137 -2.9527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8758 1.6893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4274 -0.6085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7467 -1.4656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7400 -0.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 20 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 25 1 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 35 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 2 1 1 0 0 0 17 28 1 0 0 0 0 18 3 1 1 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 31 2 0 0 0 0 19 35 1 0 0 0 0 20 29 1 0 0 0 0 21 32 2 0 0 0 0 22 7 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 30 1 6 0 0 0 24 29 1 6 0 0 0 25 30 1 6 0 0 0 26 33 1 6 0 0 0 27 26 1 1 0 0 0 27 36 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 29 5 1 6 0 0 0 30 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.3
Volume:	524.213
LogP:	4.619
LogD:	4.497
LogS:	-4.556
# Rotatable Bonds:	6
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	5.348
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.837
MDCK Permeability:	5.7652101531857625e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.181
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	85.9356918334961%
Volume Distribution (VD):	1.187
Pgp-substrate:	5.459933757781982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	6.932
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.492
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.696
Maximum Recommended Daily Dose:	0.509
Skin Sensitization:	0.925
Carcinogencity:	0.452
Eye Corrosion:	0.057
Eye Irritation:	0.025
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC96377

Natural Product ID:	NPC96377
*Common Name:**	Paraminabeolide C
IUPAC Name:	[(8R,9S,10R,13R,14S,17R)-17-[(1S,2S)-1-[(2R,3R,4R)-3,4-dimethyl-5-oxooxolan-2-yl]-1-hydroxypropan-2-yl]-10-methyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-13-yl]methyl acetate
Synonyms:	Paraminabeolide C
Standard InCHIKey:	CFLDASSGYNALJR-DYJDMTRPSA-N
Standard InCHI:	InChI=1S/C30H42O6/c1-16-17(2)28(34)36-27(16)26(33)18(3)23-8-9-25-22-7-6-20-14-21(32)10-12-29(20,5)24(22)11-13-30(23,25)15-35-19(4)31/h10,12,14,16-18,22-27,33H,6-9,11,13,15H2,1-5H3/t16-,17-,18+,22-,23-,24+,25+,26+,27-,29+,30+/m1/s1
SMILES:	CC(=O)OC[C@@]12CC[C@H]3[C@H]([C@@H]2CC[C@@H]1[C@@H]([C@@H]([C@@H]1OC(=O)[C@@H]([C@H]1C)C)O)C)CCC1=CC(=O)C=C[C@]31C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782224
PubChem CID:	53355241
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	the western coast of Pingtung county, Taiwan, at a depth of 10 m	2009-MAY	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425785]
NPO27202	Paraminabea acronocephala	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	37.9	%	PMID[520815]

☑ 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 NPC96377 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	202
0.1-0.2	1080
0.2-0.3	4569
0.3-0.4	9201
0.4-0.5	11876
0.5-0.6	5932
0.6-0.7	7012
0.7-0.8	2636
0.8-0.85	162
0.85-0.9	24
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC255309
0.9238	High Similarity	NPC471398
0.9109	High Similarity	NPC164835
0.9109	High Similarity	NPC228669
0.8922	High Similarity	NPC471293
0.8879	High Similarity	NPC474181
0.8857	High Similarity	NPC5284
0.8824	High Similarity	NPC140723
0.8788	High Similarity	NPC58052
0.8788	High Similarity	NPC111684
0.875	High Similarity	NPC59530
0.8716	High Similarity	NPC284068
0.8713	High Similarity	NPC167974
0.8679	High Similarity	NPC239097
0.8667	High Similarity	NPC19412
0.8654	High Similarity	NPC102352
0.8641	High Similarity	NPC264048
0.8624	High Similarity	NPC266728
0.8624	High Similarity	NPC49492
0.8614	High Similarity	NPC271387
0.8614	High Similarity	NPC153792
0.8614	High Similarity	NPC114274
0.8598	High Similarity	NPC231589
0.8598	High Similarity	NPC118860
0.8598	High Similarity	NPC214797
0.8585	High Similarity	NPC241927
0.8585	High Similarity	NPC258543
0.8571	High Similarity	NPC3316
0.8571	High Similarity	NPC144854
0.8544	High Similarity	NPC473163
0.8529	High Similarity	NPC218383
0.8519	High Similarity	NPC236217
0.8519	High Similarity	NPC234042
0.8519	High Similarity	NPC152117
0.8519	High Similarity	NPC170487
0.8515	High Similarity	NPC108078
0.8509	High Similarity	NPC8369
0.8505	High Similarity	NPC197428
0.8505	High Similarity	NPC37116
0.8491	Intermediate Similarity	NPC154608
0.8491	Intermediate Similarity	NPC192813
0.8491	Intermediate Similarity	NPC277017
0.8476	Intermediate Similarity	NPC470309
0.8447	Intermediate Similarity	NPC476240
0.8447	Intermediate Similarity	NPC476223
0.8447	Intermediate Similarity	NPC224720
0.844	Intermediate Similarity	NPC52634
0.844	Intermediate Similarity	NPC250109
0.844	Intermediate Similarity	NPC962
0.8411	Intermediate Similarity	NPC304495
0.8411	Intermediate Similarity	NPC153239
0.8384	Intermediate Similarity	NPC218301
0.8381	Intermediate Similarity	NPC235889
0.8381	Intermediate Similarity	NPC121566
0.8381	Intermediate Similarity	NPC100955
0.8365	Intermediate Similarity	NPC473928
0.8364	Intermediate Similarity	NPC326542
0.8351	Intermediate Similarity	NPC167877
0.835	Intermediate Similarity	NPC476274
0.8349	Intermediate Similarity	NPC71348
0.8349	Intermediate Similarity	NPC207251
0.8333	Intermediate Similarity	NPC292133
0.8333	Intermediate Similarity	NPC473627
0.8333	Intermediate Similarity	NPC475894
0.8319	Intermediate Similarity	NPC109973
0.8319	Intermediate Similarity	NPC476961
0.8319	Intermediate Similarity	NPC474585
0.8318	Intermediate Similarity	NPC469844
0.8318	Intermediate Similarity	NPC258323
0.8317	Intermediate Similarity	NPC469599
0.8304	Intermediate Similarity	NPC475913
0.8302	Intermediate Similarity	NPC63023
0.8302	Intermediate Similarity	NPC181265
0.8302	Intermediate Similarity	NPC95243
0.8302	Intermediate Similarity	NPC196528
0.83	Intermediate Similarity	NPC470224
0.8291	Intermediate Similarity	NPC473888
0.8288	Intermediate Similarity	NPC270958
0.8288	Intermediate Similarity	NPC190286
0.8286	Intermediate Similarity	NPC277074
0.8286	Intermediate Similarity	NPC95585
0.8286	Intermediate Similarity	NPC282233
0.8286	Intermediate Similarity	NPC209298
0.8283	Intermediate Similarity	NPC289213
0.8273	Intermediate Similarity	NPC255017
0.8273	Intermediate Similarity	NPC471173
0.8273	Intermediate Similarity	NPC471627
0.8269	Intermediate Similarity	NPC472924
0.8269	Intermediate Similarity	NPC252614
0.8265	Intermediate Similarity	NPC250687
0.8265	Intermediate Similarity	NPC48824
0.8265	Intermediate Similarity	NPC254572
0.8265	Intermediate Similarity	NPC229407
0.8261	Intermediate Similarity	NPC11895
0.8261	Intermediate Similarity	NPC469789
0.8241	Intermediate Similarity	NPC310546
0.8241	Intermediate Similarity	NPC41405
0.8241	Intermediate Similarity	NPC246205
0.8235	Intermediate Similarity	NPC42042
0.8235	Intermediate Similarity	NPC29410
0.8235	Intermediate Similarity	NPC200054
0.823	Intermediate Similarity	NPC474179
0.823	Intermediate Similarity	NPC473203
0.823	Intermediate Similarity	NPC475834
0.823	Intermediate Similarity	NPC475041
0.823	Intermediate Similarity	NPC161065
0.8224	Intermediate Similarity	NPC475294
0.8224	Intermediate Similarity	NPC220974
0.8224	Intermediate Similarity	NPC230541
0.8208	Intermediate Similarity	NPC96268
0.8208	Intermediate Similarity	NPC29705
0.8208	Intermediate Similarity	NPC13385
0.8208	Intermediate Similarity	NPC301787
0.82	Intermediate Similarity	NPC19114
0.82	Intermediate Similarity	NPC154101
0.82	Intermediate Similarity	NPC471747
0.8198	Intermediate Similarity	NPC243354
0.8198	Intermediate Similarity	NPC473898
0.819	Intermediate Similarity	NPC473255
0.819	Intermediate Similarity	NPC136289
0.819	Intermediate Similarity	NPC22388
0.8182	Intermediate Similarity	NPC186688
0.8182	Intermediate Similarity	NPC477943
0.8182	Intermediate Similarity	NPC280782
0.8182	Intermediate Similarity	NPC205534
0.8182	Intermediate Similarity	NPC269267
0.8174	Intermediate Similarity	NPC170538
0.8174	Intermediate Similarity	NPC222688
0.8173	Intermediate Similarity	NPC471041
0.8173	Intermediate Similarity	NPC316964
0.8173	Intermediate Similarity	NPC267921
0.8173	Intermediate Similarity	NPC287833
0.8165	Intermediate Similarity	NPC101450
0.8165	Intermediate Similarity	NPC210005
0.8165	Intermediate Similarity	NPC76084
0.8165	Intermediate Similarity	NPC5103
0.8165	Intermediate Similarity	NPC474567
0.8163	Intermediate Similarity	NPC474174
0.8163	Intermediate Similarity	NPC251808
0.8158	Intermediate Similarity	NPC79579
0.8158	Intermediate Similarity	NPC241192
0.8155	Intermediate Similarity	NPC27105
0.8148	Intermediate Similarity	NPC275539
0.8148	Intermediate Similarity	NPC472825
0.8148	Intermediate Similarity	NPC470269
0.8148	Intermediate Similarity	NPC189075
0.8144	Intermediate Similarity	NPC29447
0.8144	Intermediate Similarity	NPC470223
0.8142	Intermediate Similarity	NPC153440
0.8142	Intermediate Similarity	NPC118638
0.8137	Intermediate Similarity	NPC470016
0.8137	Intermediate Similarity	NPC317586
0.8137	Intermediate Similarity	NPC98639
0.8131	Intermediate Similarity	NPC278628
0.8131	Intermediate Similarity	NPC222833
0.8131	Intermediate Similarity	NPC231530
0.8131	Intermediate Similarity	NPC472655
0.8131	Intermediate Similarity	NPC181357
0.8125	Intermediate Similarity	NPC207217
0.8125	Intermediate Similarity	NPC251236
0.8125	Intermediate Similarity	NPC96312
0.8125	Intermediate Similarity	NPC148458
0.8125	Intermediate Similarity	NPC196931
0.8125	Intermediate Similarity	NPC176840
0.8125	Intermediate Similarity	NPC40632
0.8125	Intermediate Similarity	NPC302471
0.8125	Intermediate Similarity	NPC328374
0.8125	Intermediate Similarity	NPC270929
0.812	Intermediate Similarity	NPC174367
0.812	Intermediate Similarity	NPC293112
0.812	Intermediate Similarity	NPC47113
0.8119	Intermediate Similarity	NPC474807
0.8119	Intermediate Similarity	NPC206810
0.8119	Intermediate Similarity	NPC474736
0.8113	Intermediate Similarity	NPC474207
0.8113	Intermediate Similarity	NPC471005
0.8113	Intermediate Similarity	NPC36688
0.8113	Intermediate Similarity	NPC122811
0.8113	Intermediate Similarity	NPC474330
0.8113	Intermediate Similarity	NPC474775
0.8113	Intermediate Similarity	NPC159442
0.8108	Intermediate Similarity	NPC469463
0.8108	Intermediate Similarity	NPC469454
0.8108	Intermediate Similarity	NPC202889
0.8108	Intermediate Similarity	NPC194100
0.8108	Intermediate Similarity	NPC469496
0.8108	Intermediate Similarity	NPC194273
0.8108	Intermediate Similarity	NPC178981
0.8108	Intermediate Similarity	NPC320118
0.8108	Intermediate Similarity	NPC49451
0.8108	Intermediate Similarity	NPC317210
0.8103	Intermediate Similarity	NPC120724
0.8103	Intermediate Similarity	NPC473979
0.8095	Intermediate Similarity	NPC81530
0.8095	Intermediate Similarity	NPC101067
0.8095	Intermediate Similarity	NPC476134
0.8095	Intermediate Similarity	NPC474327
0.8091	Intermediate Similarity	NPC201992
0.8091	Intermediate Similarity	NPC188738
0.8091	Intermediate Similarity	NPC471243

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 NPC96377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1348
0.2-0.3	3927
0.3-0.4	2479
0.4-0.5	714
0.5-0.6	174
0.6-0.7	185
0.7-0.8	138
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD4632	Approved
0.82	Intermediate Similarity	NPD6079	Approved
0.819	Intermediate Similarity	NPD7492	Approved
0.8182	Intermediate Similarity	NPD8297	Approved
0.8158	Intermediate Similarity	NPD6319	Approved
0.8158	Intermediate Similarity	NPD6054	Approved
0.8148	Intermediate Similarity	NPD6899	Approved
0.8148	Intermediate Similarity	NPD6881	Approved
0.8131	Intermediate Similarity	NPD6008	Approved
0.812	Intermediate Similarity	NPD6616	Approved
0.8119	Intermediate Similarity	NPD6399	Phase 3
0.8091	Intermediate Similarity	NPD6650	Approved
0.8091	Intermediate Similarity	NPD6649	Approved
0.8056	Intermediate Similarity	NPD5697	Approved
0.8056	Intermediate Similarity	NPD6412	Phase 2
0.8053	Intermediate Similarity	NPD6009	Approved
0.8051	Intermediate Similarity	NPD7078	Approved
0.8017	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.8	Intermediate Similarity	NPD5328	Approved
0.7983	Intermediate Similarity	NPD7736	Approved
0.7982	Intermediate Similarity	NPD6011	Approved
0.7982	Intermediate Similarity	NPD7320	Approved
0.7981	Intermediate Similarity	NPD6083	Phase 2
0.7981	Intermediate Similarity	NPD6084	Phase 2
0.7963	Intermediate Similarity	NPD6402	Approved
0.7963	Intermediate Similarity	NPD7128	Approved
0.7963	Intermediate Similarity	NPD5739	Approved
0.7963	Intermediate Similarity	NPD6675	Approved
0.7949	Intermediate Similarity	NPD7604	Phase 2
0.7931	Intermediate Similarity	NPD6015	Approved
0.7931	Intermediate Similarity	NPD6016	Approved
0.7931	Intermediate Similarity	NPD5983	Phase 2
0.7928	Intermediate Similarity	NPD8130	Phase 1
0.7928	Intermediate Similarity	NPD6617	Approved
0.7928	Intermediate Similarity	NPD6869	Approved
0.7928	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD6014	Approved
0.7909	Intermediate Similarity	NPD6012	Approved
0.7909	Intermediate Similarity	NPD6373	Approved
0.7909	Intermediate Similarity	NPD6372	Approved
0.7909	Intermediate Similarity	NPD6013	Approved
0.79	Intermediate Similarity	NPD6903	Approved
0.79	Intermediate Similarity	NPD6672	Approved
0.79	Intermediate Similarity	NPD5737	Approved
0.7895	Intermediate Similarity	NPD7115	Discovery
0.7885	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5221	Approved
0.7885	Intermediate Similarity	NPD5222	Approved
0.7879	Intermediate Similarity	NPD7521	Approved
0.7879	Intermediate Similarity	NPD7334	Approved
0.7879	Intermediate Similarity	NPD6409	Approved
0.7879	Intermediate Similarity	NPD7146	Approved
0.7879	Intermediate Similarity	NPD5330	Approved
0.7879	Intermediate Similarity	NPD6684	Approved
0.7863	Intermediate Similarity	NPD5988	Approved
0.7857	Intermediate Similarity	NPD6882	Approved
0.7845	Intermediate Similarity	NPD6059	Approved
0.7815	Intermediate Similarity	NPD6336	Discontinued
0.781	Intermediate Similarity	NPD5173	Approved
0.7788	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD8293	Discontinued
0.7736	Intermediate Similarity	NPD5696	Approved
0.7736	Intermediate Similarity	NPD7638	Approved
0.7727	Intermediate Similarity	NPD5701	Approved
0.7723	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4697	Phase 3
0.77	Intermediate Similarity	NPD3618	Phase 1
0.7679	Intermediate Similarity	NPD4634	Approved
0.7677	Intermediate Similarity	NPD3665	Phase 1
0.7677	Intermediate Similarity	NPD3133	Approved
0.7677	Intermediate Similarity	NPD3666	Approved
0.7677	Intermediate Similarity	NPD4786	Approved
0.7664	Intermediate Similarity	NPD7640	Approved
0.7664	Intermediate Similarity	NPD7639	Approved
0.7664	Intermediate Similarity	NPD5285	Approved
0.7664	Intermediate Similarity	NPD5286	Approved
0.7664	Intermediate Similarity	NPD4696	Approved
0.7658	Intermediate Similarity	NPD6686	Approved
0.7652	Intermediate Similarity	NPD6868	Approved
0.7627	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4629	Approved
0.7619	Intermediate Similarity	NPD5695	Phase 3
0.7619	Intermediate Similarity	NPD5210	Approved
0.7611	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5223	Approved
0.7573	Intermediate Similarity	NPD5207	Approved
0.7524	Intermediate Similarity	NPD7748	Approved
0.7523	Intermediate Similarity	NPD5224	Approved
0.7523	Intermediate Similarity	NPD5211	Phase 2
0.7523	Intermediate Similarity	NPD5225	Approved
0.7523	Intermediate Similarity	NPD5226	Approved
0.7523	Intermediate Similarity	NPD4633	Approved
0.7521	Intermediate Similarity	NPD7507	Approved
0.7521	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.7477	Intermediate Similarity	NPD4755	Approved
0.7477	Intermediate Similarity	NPD7902	Approved
0.7476	Intermediate Similarity	NPD6080	Approved
0.7476	Intermediate Similarity	NPD6673	Approved
0.7476	Intermediate Similarity	NPD4753	Phase 2
0.7476	Intermediate Similarity	NPD6904	Approved
0.7475	Intermediate Similarity	NPD3667	Approved
0.7458	Intermediate Similarity	NPD7101	Approved
0.7458	Intermediate Similarity	NPD7100	Approved
0.7455	Intermediate Similarity	NPD5175	Approved
0.7455	Intermediate Similarity	NPD5174	Approved
0.7436	Intermediate Similarity	NPD6317	Approved
0.7398	Intermediate Similarity	NPD6033	Approved
0.7391	Intermediate Similarity	NPD6053	Discontinued
0.7387	Intermediate Similarity	NPD5141	Approved
0.7373	Intermediate Similarity	NPD6314	Approved
0.7373	Intermediate Similarity	NPD6313	Approved
0.7358	Intermediate Similarity	NPD6001	Approved
0.7355	Intermediate Similarity	NPD8328	Phase 3
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.735	Intermediate Similarity	NPD6274	Approved
0.7339	Intermediate Similarity	NPD4700	Approved
0.7339	Intermediate Similarity	NPD7319	Approved
0.73	Intermediate Similarity	NPD4223	Phase 3
0.73	Intermediate Similarity	NPD4221	Approved
0.7282	Intermediate Similarity	NPD3573	Approved
0.7264	Intermediate Similarity	NPD4202	Approved
0.7255	Intermediate Similarity	NPD5329	Approved
0.7248	Intermediate Similarity	NPD4225	Approved
0.7213	Intermediate Similarity	NPD6067	Discontinued
0.7212	Intermediate Similarity	NPD5208	Approved
0.7196	Intermediate Similarity	NPD7900	Approved
0.7196	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5168	Approved
0.7193	Intermediate Similarity	NPD4729	Approved
0.7193	Intermediate Similarity	NPD4730	Approved
0.7193	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5690	Phase 2
0.7184	Intermediate Similarity	NPD6098	Approved
0.7184	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD8034	Phase 2
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5694	Approved
0.717	Intermediate Similarity	NPD8035	Phase 2
0.717	Intermediate Similarity	NPD5693	Phase 1
0.7157	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD5956	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD6052	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7260	Phase 2
0.7087	Intermediate Similarity	NPD1694	Approved
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7069	Intermediate Similarity	NPD5250	Approved
0.7069	Intermediate Similarity	NPD5249	Phase 3
0.7069	Intermediate Similarity	NPD5251	Approved
0.7069	Intermediate Similarity	NPD5169	Approved
0.7069	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5247	Approved
0.7069	Intermediate Similarity	NPD5248	Approved
0.7069	Intermediate Similarity	NPD5135	Approved
0.7059	Intermediate Similarity	NPD4788	Approved
0.7054	Intermediate Similarity	NPD7632	Discontinued
0.7049	Intermediate Similarity	NPD6908	Approved
0.7049	Intermediate Similarity	NPD7503	Approved
0.7049	Intermediate Similarity	NPD6909	Approved
0.7043	Intermediate Similarity	NPD5128	Approved
0.7019	Intermediate Similarity	NPD4138	Approved
0.7019	Intermediate Similarity	NPD4693	Phase 3
0.7019	Intermediate Similarity	NPD4689	Approved
0.7019	Intermediate Similarity	NPD4690	Approved
0.7019	Intermediate Similarity	NPD5205	Approved
0.7019	Intermediate Similarity	NPD4688	Approved
0.7018	Intermediate Similarity	NPD4767	Approved
0.7018	Intermediate Similarity	NPD4768	Approved
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD7637	Suspended
0.7009	Intermediate Similarity	NPD5217	Approved
0.7009	Intermediate Similarity	NPD5216	Approved
0.7	Intermediate Similarity	NPD4195	Approved
0.699	Remote Similarity	NPD3668	Phase 3
0.6981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6101	Approved
0.6961	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6435	Approved
0.6957	Remote Similarity	NPD6614	Approved
0.6944	Remote Similarity	NPD5778	Approved
0.6944	Remote Similarity	NPD5779	Approved
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6931	Remote Similarity	NPD4695	Discontinued
0.6923	Remote Similarity	NPD6371	Approved
0.6923	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5785	Approved
0.69	Remote Similarity	NPD5784	Clinical (unspecified phase)

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