NPASS Compound

Structure

CID29705 OpenBabel06191715352D 36 39 0 0 1 0 0 0 0 0999 V2000 -1.2119 7.3984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8947 7.2211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0072 5.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9048 4.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9319 2.2422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 1.9918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8479 3.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6899 5.2781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5875 4.3066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3862 0.9789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5397 1.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5400 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0021 6.8240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8997 5.8525 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6949 3.9095 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9603 2.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3865 0.0010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8473 1.4666 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6938 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8462 2.4444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5402 2.4434 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6947 2.9326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8465 1.4671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8470 -0.4887 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 1.6935 0.9784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 2.4439 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5624 1.2485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2551 -0.5001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7145 2.9460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8659 -0.5003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3865 2.9314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 5 18 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 29 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 16 3 1 1 0 0 0 17 4 1 1 0 0 0 17 25 1 0 0 0 0 18 31 2 0 0 0 0 18 36 1 0 0 0 0 19 32 1 6 0 0 0 20 24 1 0 0 0 0 20 30 1 6 0 0 0 21 27 1 0 0 0 0 21 29 1 6 0 0 0 22 26 1 0 0 0 0 22 33 1 6 0 0 0 23 25 1 0 0 0 0 23 36 1 6 0 0 0 24 26 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 34 2 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.35
Volume:	538.042
LogP:	4.316
LogD:	3.189
LogS:	-3.603
# Rotatable Bonds:	6
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	5.401
Fsp3:	0.867
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:	-4.904
MDCK Permeability:	8.082364365691319e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.42
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.592
Plasma Protein Binding (PPB):	82.79180145263672%
Volume Distribution (VD):	0.806
Pgp-substrate:	5.0245208740234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.669

ADMET: Excretion

Clearance (CL):	4.753
Half-life (T1/2):	0.469

ADMET: Toxicity

hERG Blockers:	0.202
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.141
Carcinogencity:	0.053
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC29705

Natural Product ID:	NPC29705
*Common Name:**	Anicequol
IUPAC Name:	[(3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,7,11-trihydroxy-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms:	Anicequol
Standard InCHIKey:	LWMKDRSIMLTGDK-TZEVRYHJSA-N
Standard InCHI:	InChI=1S/C30H48O6/c1-15(2)16(3)8-9-17(4)25-23(36-18(5)31)13-20-24-26(22(33)14-30(20,25)7)29(6)11-10-19(32)12-21(29)27(34)28(24)35/h8-9,15-17,19-26,28,32-33,35H,10-14H2,1-7H3/b9-8+/t16-,17+,19-,20-,21+,22-,23-,24-,25-,26-,28+,29-,30-/m0/s1
SMILES:	CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1[C@H](C[C@H]2[C@H]3[C@H]([C@H](C[C@]12C)O)[C@@]1(C)CC[C@@H](C[C@@H]1C(=O)[C@@H]3O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1770668
PubChem CID:	10413810
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193025]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19255	Necturus maculosus	Species	Proteidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19725	Garcinia vilersiana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289.1	Heracleum sphondylium subsp. pyrenaicum	Subspecies	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18943	Dorstenia excentrica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19529	Astrotrichilia asterotricha	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2988	Peteravenia schultzii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17981	Melolontha vulgaris	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19452	Gaillardia pinnatifida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18452	Haplophyton cimicidum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22603	Synedrellopsis grisebachii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19725	Garcinia vilersiana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13440	Enterolobium cyclocarpum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16824	Cryptocarya oubatchensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10435	Aphis serpylli	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19194	Licaria rigida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19954	Conogethes punctiferalis	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19255	Necturus maculosus	Species	Proteidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289.1	Heracleum sphondylium subsp. pyrenaicum	Subspecies	Apiaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	6.0	mm	PMID[544002]

☑ 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 NPC29705 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	200
0.1-0.2	1331
0.2-0.3	4964
0.3-0.4	10203
0.4-0.5	11100
0.5-0.6	5928
0.6-0.7	5291
0.7-0.8	3340
0.8-0.85	289
0.85-0.9	43
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9307	High Similarity	NPC94529
0.9109	High Similarity	NPC278628
0.9109	High Similarity	NPC231530
0.91	High Similarity	NPC140723
0.9091	High Similarity	NPC477052
0.9091	High Similarity	NPC477051
0.9091	High Similarity	NPC477053
0.9	High Similarity	NPC477054
0.8952	High Similarity	NPC71348
0.8922	High Similarity	NPC196528
0.8889	High Similarity	NPC477854
0.8879	High Similarity	NPC270958
0.8868	High Similarity	NPC202889
0.8824	High Similarity	NPC47281
0.88	High Similarity	NPC218383
0.88	High Similarity	NPC15390
0.8774	High Similarity	NPC280782
0.8762	High Similarity	NPC197428
0.8738	High Similarity	NPC475571
0.8738	High Similarity	NPC50535
0.8738	High Similarity	NPC28791
0.8725	High Similarity	NPC469985
0.8716	High Similarity	NPC118638
0.8713	High Similarity	NPC253886
0.8713	High Similarity	NPC121218
0.8687	High Similarity	NPC29410
0.8687	High Similarity	NPC200054
0.8687	High Similarity	NPC477853
0.8679	High Similarity	NPC214797
0.8679	High Similarity	NPC118860
0.8679	High Similarity	NPC231589
0.8667	High Similarity	NPC258543
0.8667	High Similarity	NPC241927
0.8654	High Similarity	NPC86852
0.8654	High Similarity	NPC44063
0.8654	High Similarity	NPC251824
0.8627	High Similarity	NPC170615
0.8627	High Similarity	NPC22388
0.86	High Similarity	NPC190554
0.8598	High Similarity	NPC170487
0.8586	High Similarity	NPC279974
0.8586	High Similarity	NPC469599
0.8586	High Similarity	NPC98639
0.8571	High Similarity	NPC470376
0.8571	High Similarity	NPC211224
0.8571	High Similarity	NPC470375
0.8519	High Similarity	NPC962
0.8519	High Similarity	NPC52634
0.8515	High Similarity	NPC162459
0.8515	High Similarity	NPC20479
0.8515	High Similarity	NPC119036
0.8515	High Similarity	NPC38296
0.8515	High Similarity	NPC471038
0.8515	High Similarity	NPC38471
0.8515	High Similarity	NPC98837
0.8515	High Similarity	NPC28864
0.8505	High Similarity	NPC470281
0.85	High Similarity	NPC173272
0.85	High Similarity	NPC49371
0.8491	Intermediate Similarity	NPC2766
0.8469	Intermediate Similarity	NPC154101
0.8462	Intermediate Similarity	NPC310586
0.8462	Intermediate Similarity	NPC96268
0.8462	Intermediate Similarity	NPC235889
0.8447	Intermediate Similarity	NPC15396
0.8447	Intermediate Similarity	NPC193934
0.8447	Intermediate Similarity	NPC271980
0.8431	Intermediate Similarity	NPC293866
0.84	Intermediate Similarity	NPC48330
0.84	Intermediate Similarity	NPC69548
0.84	Intermediate Similarity	NPC184848
0.8393	Intermediate Similarity	NPC109973
0.8384	Intermediate Similarity	NPC224060
0.8384	Intermediate Similarity	NPC244356
0.8381	Intermediate Similarity	NPC181265
0.8381	Intermediate Similarity	NPC295366
0.8381	Intermediate Similarity	NPC37600
0.8365	Intermediate Similarity	NPC222153
0.8365	Intermediate Similarity	NPC191892
0.8365	Intermediate Similarity	NPC159442
0.8365	Intermediate Similarity	NPC87927
0.8364	Intermediate Similarity	NPC49492
0.8364	Intermediate Similarity	NPC266728
0.835	Intermediate Similarity	NPC295276
0.835	Intermediate Similarity	NPC52899
0.835	Intermediate Similarity	NPC474327
0.835	Intermediate Similarity	NPC46848
0.835	Intermediate Similarity	NPC252614
0.835	Intermediate Similarity	NPC289148
0.835	Intermediate Similarity	NPC163963
0.8349	Intermediate Similarity	NPC194100
0.8349	Intermediate Similarity	NPC250109
0.8333	Intermediate Similarity	NPC89099
0.8333	Intermediate Similarity	NPC153792
0.8333	Intermediate Similarity	NPC271387
0.8333	Intermediate Similarity	NPC477813
0.8333	Intermediate Similarity	NPC191565
0.8333	Intermediate Similarity	NPC474724
0.8333	Intermediate Similarity	NPC114274
0.8318	Intermediate Similarity	NPC304495
0.8317	Intermediate Similarity	NPC42042
0.8317	Intermediate Similarity	NPC329910
0.8317	Intermediate Similarity	NPC304899
0.8317	Intermediate Similarity	NPC253115
0.8317	Intermediate Similarity	NPC219353
0.8302	Intermediate Similarity	NPC144854
0.8302	Intermediate Similarity	NPC3316
0.8302	Intermediate Similarity	NPC201908
0.8302	Intermediate Similarity	NPC176949
0.8302	Intermediate Similarity	NPC59530
0.83	Intermediate Similarity	NPC111015
0.8286	Intermediate Similarity	NPC471293
0.8286	Intermediate Similarity	NPC477812
0.8283	Intermediate Similarity	NPC198054
0.8283	Intermediate Similarity	NPC23434
0.8269	Intermediate Similarity	NPC286519
0.8269	Intermediate Similarity	NPC246736
0.8269	Intermediate Similarity	NPC136289
0.8269	Intermediate Similarity	NPC275990
0.8269	Intermediate Similarity	NPC88203
0.8269	Intermediate Similarity	NPC304832
0.8269	Intermediate Similarity	NPC214946
0.8269	Intermediate Similarity	NPC76866
0.8269	Intermediate Similarity	NPC148628
0.8265	Intermediate Similarity	NPC474679
0.8261	Intermediate Similarity	NPC473255
0.8252	Intermediate Similarity	NPC83709
0.8252	Intermediate Similarity	NPC144956
0.8252	Intermediate Similarity	NPC108371
0.8252	Intermediate Similarity	NPC287676
0.8246	Intermediate Similarity	NPC222688
0.8246	Intermediate Similarity	NPC65858
0.8235	Intermediate Similarity	NPC108078
0.8235	Intermediate Similarity	NPC107243
0.8235	Intermediate Similarity	NPC57416
0.8235	Intermediate Similarity	NPC10864
0.8235	Intermediate Similarity	NPC18509
0.8224	Intermediate Similarity	NPC277017
0.8224	Intermediate Similarity	NPC469845
0.8224	Intermediate Similarity	NPC470269
0.8224	Intermediate Similarity	NPC163216
0.8224	Intermediate Similarity	NPC154608
0.8224	Intermediate Similarity	NPC192813
0.8218	Intermediate Similarity	NPC45324
0.8218	Intermediate Similarity	NPC470229
0.8218	Intermediate Similarity	NPC470232
0.8218	Intermediate Similarity	NPC222845
0.8218	Intermediate Similarity	NPC162001
0.8214	Intermediate Similarity	NPC324253
0.8208	Intermediate Similarity	NPC265127
0.8208	Intermediate Similarity	NPC96377
0.82	Intermediate Similarity	NPC294263
0.82	Intermediate Similarity	NPC476189
0.82	Intermediate Similarity	NPC470224
0.82	Intermediate Similarity	NPC141497
0.82	Intermediate Similarity	NPC206810
0.82	Intermediate Similarity	NPC107674
0.82	Intermediate Similarity	NPC477855
0.82	Intermediate Similarity	NPC170220
0.8198	Intermediate Similarity	NPC298278
0.8198	Intermediate Similarity	NPC148458
0.8198	Intermediate Similarity	NPC196931
0.819	Intermediate Similarity	NPC312900
0.819	Intermediate Similarity	NPC95585
0.819	Intermediate Similarity	NPC275583
0.819	Intermediate Similarity	NPC266
0.819	Intermediate Similarity	NPC282233
0.819	Intermediate Similarity	NPC277074
0.819	Intermediate Similarity	NPC209298
0.819	Intermediate Similarity	NPC122811
0.819	Intermediate Similarity	NPC117185
0.8182	Intermediate Similarity	NPC100313
0.8182	Intermediate Similarity	NPC471896
0.8174	Intermediate Similarity	NPC43252
0.8174	Intermediate Similarity	NPC135038
0.8173	Intermediate Similarity	NPC224720
0.8173	Intermediate Similarity	NPC476240
0.8173	Intermediate Similarity	NPC476223
0.8173	Intermediate Similarity	NPC81530
0.8165	Intermediate Similarity	NPC43775
0.8163	Intermediate Similarity	NPC193360
0.8155	Intermediate Similarity	NPC474793
0.8155	Intermediate Similarity	NPC58942
0.8155	Intermediate Similarity	NPC260149
0.8155	Intermediate Similarity	NPC78427
0.8155	Intermediate Similarity	NPC16911
0.8148	Intermediate Similarity	NPC285298
0.8148	Intermediate Similarity	NPC257082
0.8148	Intermediate Similarity	NPC141350
0.8142	Intermediate Similarity	NPC475041
0.8142	Intermediate Similarity	NPC473203
0.8137	Intermediate Similarity	NPC234564
0.8137	Intermediate Similarity	NPC305483
0.8137	Intermediate Similarity	NPC96859
0.8137	Intermediate Similarity	NPC328162
0.8136	Intermediate Similarity	NPC221414
0.8131	Intermediate Similarity	NPC220974
0.8131	Intermediate Similarity	NPC165873
0.8131	Intermediate Similarity	NPC263729
0.8125	Intermediate Similarity	NPC471854

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 NPC29705 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	1601
0.2-0.3	4006
0.3-0.4	2202
0.4-0.5	657
0.5-0.6	185
0.6-0.7	159
0.7-0.8	126
0.8-0.85	37
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6881	Approved
0.875	High Similarity	NPD6899	Approved
0.8738	High Similarity	NPD6675	Approved
0.8738	High Similarity	NPD6402	Approved
0.8738	High Similarity	NPD7128	Approved
0.8738	High Similarity	NPD5739	Approved
0.8679	High Similarity	NPD6650	Approved
0.8679	High Similarity	NPD6649	Approved
0.8667	High Similarity	NPD6372	Approved
0.8667	High Similarity	NPD6373	Approved
0.8654	High Similarity	NPD5697	Approved
0.8585	High Similarity	NPD7290	Approved
0.8585	High Similarity	NPD6883	Approved
0.8585	High Similarity	NPD7102	Approved
0.8571	High Similarity	NPD6011	Approved
0.8571	High Similarity	NPD7320	Approved
0.8519	High Similarity	NPD4632	Approved
0.8505	High Similarity	NPD6847	Approved
0.8505	High Similarity	NPD8130	Phase 1
0.8505	High Similarity	NPD6869	Approved
0.8505	High Similarity	NPD6617	Approved
0.8491	Intermediate Similarity	NPD6014	Approved
0.8491	Intermediate Similarity	NPD6013	Approved
0.8491	Intermediate Similarity	NPD6012	Approved
0.8476	Intermediate Similarity	NPD5701	Approved
0.8426	Intermediate Similarity	NPD6882	Approved
0.8426	Intermediate Similarity	NPD8297	Approved
0.8333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD6009	Approved
0.8252	Intermediate Similarity	NPD4696	Approved
0.8252	Intermediate Similarity	NPD5286	Approved
0.8252	Intermediate Similarity	NPD5285	Approved
0.8235	Intermediate Similarity	NPD4755	Approved
0.823	Intermediate Similarity	NPD6319	Approved
0.8208	Intermediate Similarity	NPD6008	Approved
0.82	Intermediate Similarity	NPD6399	Phase 3
0.8174	Intermediate Similarity	NPD7604	Phase 2
0.8173	Intermediate Similarity	NPD5223	Approved
0.8158	Intermediate Similarity	NPD5983	Phase 2
0.8155	Intermediate Similarity	NPD7638	Approved
0.8103	Intermediate Similarity	NPD7492	Approved
0.8095	Intermediate Similarity	NPD5226	Approved
0.8095	Intermediate Similarity	NPD5225	Approved
0.8095	Intermediate Similarity	NPD5224	Approved
0.8095	Intermediate Similarity	NPD5211	Phase 2
0.8095	Intermediate Similarity	NPD4633	Approved
0.8077	Intermediate Similarity	NPD7640	Approved
0.8077	Intermediate Similarity	NPD4700	Approved
0.8077	Intermediate Similarity	NPD7639	Approved
0.807	Intermediate Similarity	NPD6054	Approved
0.8058	Intermediate Similarity	NPD6083	Phase 2
0.8058	Intermediate Similarity	NPD6084	Phase 2
0.8053	Intermediate Similarity	NPD6335	Approved
0.8051	Intermediate Similarity	NPD7736	Approved
0.8034	Intermediate Similarity	NPD6616	Approved
0.8034	Intermediate Similarity	NPD6336	Discontinued
0.8019	Intermediate Similarity	NPD5174	Approved
0.8019	Intermediate Similarity	NPD5175	Approved
0.7982	Intermediate Similarity	NPD7100	Approved
0.7982	Intermediate Similarity	NPD7101	Approved
0.7966	Intermediate Similarity	NPD7078	Approved
0.7965	Intermediate Similarity	NPD6317	Approved
0.7961	Intermediate Similarity	NPD4697	Phase 3
0.7961	Intermediate Similarity	NPD5221	Approved
0.7961	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5222	Approved
0.7944	Intermediate Similarity	NPD5141	Approved
0.7931	Intermediate Similarity	NPD6370	Approved
0.7921	Intermediate Similarity	NPD8034	Phase 2
0.7921	Intermediate Similarity	NPD6079	Approved
0.7921	Intermediate Similarity	NPD8035	Phase 2
0.7913	Intermediate Similarity	NPD6059	Approved
0.7909	Intermediate Similarity	NPD4634	Approved
0.79	Intermediate Similarity	NPD5328	Approved
0.7895	Intermediate Similarity	NPD6314	Approved
0.7895	Intermediate Similarity	NPD6313	Approved
0.7885	Intermediate Similarity	NPD5173	Approved
0.7876	Intermediate Similarity	NPD6274	Approved
0.785	Intermediate Similarity	NPD4754	Approved
0.7845	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6015	Approved
0.7845	Intermediate Similarity	NPD6016	Approved
0.7815	Intermediate Similarity	NPD8293	Discontinued
0.781	Intermediate Similarity	NPD5696	Approved
0.7778	Intermediate Similarity	NPD5988	Approved
0.7727	Intermediate Similarity	NPD4729	Approved
0.7727	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4730	Approved
0.7719	Intermediate Similarity	NPD6868	Approved
0.7714	Intermediate Similarity	NPD7902	Approved
0.7706	Intermediate Similarity	NPD4767	Approved
0.7706	Intermediate Similarity	NPD4768	Approved
0.7692	Intermediate Similarity	NPD6909	Approved
0.7692	Intermediate Similarity	NPD6908	Approved
0.7692	Intermediate Similarity	NPD5695	Phase 3
0.7677	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4202	Approved
0.7624	Intermediate Similarity	NPD5737	Approved
0.7624	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6672	Approved
0.76	Intermediate Similarity	NPD6098	Approved
0.76	Intermediate Similarity	NPD6684	Approved
0.76	Intermediate Similarity	NPD6409	Approved
0.76	Intermediate Similarity	NPD7334	Approved
0.76	Intermediate Similarity	NPD7146	Approved
0.76	Intermediate Similarity	NPD7521	Approved
0.76	Intermediate Similarity	NPD3618	Phase 1
0.76	Intermediate Similarity	NPD5330	Approved
0.7596	Intermediate Similarity	NPD7748	Approved
0.7589	Intermediate Similarity	NPD5249	Phase 3
0.7589	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5248	Approved
0.7589	Intermediate Similarity	NPD5247	Approved
0.7589	Intermediate Similarity	NPD5251	Approved
0.7589	Intermediate Similarity	NPD5250	Approved
0.7589	Intermediate Similarity	NPD5135	Approved
0.7589	Intermediate Similarity	NPD5169	Approved
0.7583	Intermediate Similarity	NPD7507	Approved
0.7576	Intermediate Similarity	NPD4786	Approved
0.7573	Intermediate Similarity	NPD7515	Phase 2
0.7568	Intermediate Similarity	NPD5128	Approved
0.7551	Intermediate Similarity	NPD6435	Approved
0.7549	Intermediate Similarity	NPD6904	Approved
0.7549	Intermediate Similarity	NPD6080	Approved
0.7549	Intermediate Similarity	NPD4753	Phase 2
0.7549	Intermediate Similarity	NPD6673	Approved
0.7524	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5210	Approved
0.7524	Intermediate Similarity	NPD4629	Approved
0.7522	Intermediate Similarity	NPD5216	Approved
0.7522	Intermediate Similarity	NPD5215	Approved
0.7522	Intermediate Similarity	NPD5217	Approved
0.7522	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.7477	Intermediate Similarity	NPD6412	Phase 2
0.7459	Intermediate Similarity	NPD6033	Approved
0.7451	Intermediate Similarity	NPD6903	Approved
0.7431	Intermediate Similarity	NPD7632	Discontinued
0.7429	Intermediate Similarity	NPD7900	Approved
0.7429	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8328	Phase 3
0.7404	Intermediate Similarity	NPD5284	Approved
0.7404	Intermediate Similarity	NPD5281	Approved
0.74	Intermediate Similarity	NPD3665	Phase 1
0.74	Intermediate Similarity	NPD3133	Approved
0.74	Intermediate Similarity	NPD3666	Approved
0.7398	Intermediate Similarity	NPD7319	Approved
0.7396	Intermediate Similarity	NPD6116	Phase 1
0.7374	Intermediate Similarity	NPD3667	Approved
0.7347	Intermediate Similarity	NPD5368	Approved
0.7347	Intermediate Similarity	NPD7525	Registered
0.7328	Intermediate Similarity	NPD5167	Approved
0.7327	Intermediate Similarity	NPD5329	Approved
0.7292	Intermediate Similarity	NPD6117	Approved
0.7257	Intermediate Similarity	NPD5168	Approved
0.7238	Intermediate Similarity	NPD5693	Phase 1
0.7238	Intermediate Similarity	NPD6050	Approved
0.7238	Intermediate Similarity	NPD5694	Approved
0.7228	Intermediate Similarity	NPD4197	Approved
0.7209	Intermediate Similarity	NPD6333	Approved
0.7209	Intermediate Similarity	NPD6334	Approved
0.7203	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD3703	Phase 2
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7129	Intermediate Similarity	NPD4788	Approved
0.7103	Intermediate Similarity	NPD6001	Approved
0.71	Intermediate Similarity	NPD5369	Approved
0.7087	Intermediate Similarity	NPD5690	Phase 2
0.7087	Intermediate Similarity	NPD5786	Approved
0.7087	Intermediate Similarity	NPD5279	Phase 3
0.7083	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6411	Approved
0.7043	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4223	Phase 3
0.703	Intermediate Similarity	NPD4221	Approved
0.7019	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD7327	Approved
0.6992	Remote Similarity	NPD6067	Discontinued
0.6981	Remote Similarity	NPD5207	Approved
0.697	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6921	Approved
0.6952	Remote Similarity	NPD5208	Approved
0.6949	Remote Similarity	NPD8133	Approved
0.6942	Remote Similarity	NPD7516	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4694	Approved
0.6923	Remote Similarity	NPD5280	Approved
0.6916	Remote Similarity	NPD7637	Suspended
0.6893	Remote Similarity	NPD3668	Phase 3
0.6887	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6101	Approved
0.6885	Remote Similarity	NPD8377	Approved
0.6885	Remote Similarity	NPD8294	Approved
0.6875	Remote Similarity	NPD4809	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