NPASS Compound

Structure

CID254071 OpenBabel06191716052D 47 52 0 0 1 0 0 0 0 0999 V2000 3.0976 3.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5033 -3.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9997 -2.8523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0093 1.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8766 0.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8799 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0642 1.4018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0708 -0.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2552 0.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6599 1.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2198 0.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9525 1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5124 1.4441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4413 -1.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6405 -0.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6959 2.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3598 3.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2585 -0.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2935 0.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8788 2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4478 -0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5863 3.0947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6273 -1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8265 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4694 2.5765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6470 -1.8832 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6404 -0.9471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8199 -1.4201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8205 -2.3672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4577 -2.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2358 1.5400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3454 1.0343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0002 -1.8936 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8201 -0.4735 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1873 3.1072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 4.1186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8235 -3.3492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1684 -3.2415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4908 -2.7440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1714 3.0484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6201 -2.9178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3733 -2.1566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1190 1.0218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2430 2.5640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3382 0.0103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4622 1.5525 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 40 1 0 0 0 0 2 41 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 2 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 24 2 0 0 0 0 16 22 1 0 0 0 0 16 35 1 0 0 0 0 17 25 1 0 0 0 0 17 44 1 0 0 0 0 18 27 1 0 0 0 0 20 40 1 0 0 0 0 21 45 1 0 0 0 0 22 36 1 1 0 0 0 23 28 2 0 0 0 0 23 41 1 0 0 0 0 24 28 1 0 0 0 0 24 47 1 0 0 0 0 25 22 1 6 0 0 0 25 46 1 0 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 1 0 0 0 27 34 1 6 0 0 0 28 33 1 0 0 0 0 29 33 1 1 0 0 0 29 37 1 0 0 0 0 30 38 2 0 0 0 0 30 42 1 0 0 0 0 31 32 1 0 0 0 0 31 43 1 6 0 0 0 31 44 1 0 0 0 0 32 45 1 1 0 0 0 32 46 1 0 0 0 0 33 34 1 6 0 0 0 33 39 1 0 0 0 0 34 19 1 6 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.23
Volume:	633.19
LogP:	2.461
LogD:	2.437
LogS:	-4.418
# Rotatable Bonds:	11
TPSA:	171.83
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.233
Synthetic Accessibility Score:	4.954
Fsp3:	0.441
Lipinski Rule-of-5:	Rejected
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:	-5.877
MDCK Permeability:	4.4048090785508975e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	77.61363983154297%
Volume Distribution (VD):	0.462
Pgp-substrate:	11.94548511505127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.737
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.716

ADMET: Excretion

Clearance (CL):	7.156
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.599
Drug-inuced Liver Injury (DILI):	0.818
AMES Toxicity:	0.779
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.051
Carcinogencity:	0.874
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.089

Download Data

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

Natural Product: NPC254071

Natural Product ID:	NPC254071
*Common Name:**	2'-Episilvestrol
IUPAC Name:	methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
Synonyms:	2''-Episilvestrol
Standard InCHIKey:	GVKXFVCXBFGBCD-JRPGFILLSA-N
Standard InCHI:	InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25+,26+,27+,29+,31+,32+,33-,34-/m0/s1
SMILES:	COc1ccc(cc1)[C@]12[C@H](c3ccccc3)[C@H]([C@H]([C@]1(c1c(cc(cc1O2)O[C@H]1[C@H](OC)OC[C@H]([C@H](CO)O)O1)OC)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651036
PubChem CID:	11467934
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

*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
NPO23098	Aglaia silvestris	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[15132542]
NPO23098	Aglaia silvestris	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15132542]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22817615]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23098	Aglaia silvestris	Species	Meliaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.001	uM	PMID[504012]

☑ 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 NPC254071 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	360
0.1-0.2	1392
0.2-0.3	3048
0.3-0.4	6233
0.4-0.5	10479
0.5-0.6	7668
0.6-0.7	7274
0.7-0.8	5954
0.8-0.85	270
0.85-0.9	4
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271755
1.0	High Similarity	NPC149502
1.0	High Similarity	NPC222665
0.9437	High Similarity	NPC73422
0.9437	High Similarity	NPC310399
0.9379	High Similarity	NPC90336
0.9375	High Similarity	NPC209473
0.9375	High Similarity	NPC329743
0.9226	High Similarity	NPC23593
0.9167	High Similarity	NPC107739
0.9118	High Similarity	NPC236089
0.9112	High Similarity	NPC263955
0.9059	High Similarity	NPC29587
0.9036	High Similarity	NPC475621
0.8688	High Similarity	NPC20360
0.8476	Intermediate Similarity	NPC475379
0.8457	Intermediate Similarity	NPC469700
0.8439	Intermediate Similarity	NPC76047
0.8438	Intermediate Similarity	NPC184607
0.8427	Intermediate Similarity	NPC106700
0.8421	Intermediate Similarity	NPC318472
0.8421	Intermediate Similarity	NPC222531
0.8415	Intermediate Similarity	NPC107197
0.8398	Intermediate Similarity	NPC308709
0.8375	Intermediate Similarity	NPC470937
0.8363	Intermediate Similarity	NPC327694
0.8362	Intermediate Similarity	NPC179862
0.8343	Intermediate Similarity	NPC168789
0.8343	Intermediate Similarity	NPC195972
0.8343	Intermediate Similarity	NPC308265
0.8343	Intermediate Similarity	NPC43761
0.8342	Intermediate Similarity	NPC258128
0.8333	Intermediate Similarity	NPC127406
0.8333	Intermediate Similarity	NPC189730
0.8333	Intermediate Similarity	NPC294863
0.8333	Intermediate Similarity	NPC282636
0.8333	Intermediate Similarity	NPC475378
0.8324	Intermediate Similarity	NPC249977
0.8323	Intermediate Similarity	NPC160882
0.8315	Intermediate Similarity	NPC469371
0.8314	Intermediate Similarity	NPC7752
0.8314	Intermediate Similarity	NPC72016
0.8314	Intermediate Similarity	NPC475979
0.8314	Intermediate Similarity	NPC294722
0.8305	Intermediate Similarity	NPC206061
0.8304	Intermediate Similarity	NPC472876
0.8304	Intermediate Similarity	NPC93215
0.8304	Intermediate Similarity	NPC310603
0.8303	Intermediate Similarity	NPC240592
0.8303	Intermediate Similarity	NPC117346
0.8294	Intermediate Similarity	NPC200708
0.8294	Intermediate Similarity	NPC271479
0.8286	Intermediate Similarity	NPC470685
0.8284	Intermediate Similarity	NPC122809
0.8284	Intermediate Similarity	NPC43638
0.8274	Intermediate Similarity	NPC164152
0.8268	Intermediate Similarity	NPC199172
0.8268	Intermediate Similarity	NPC186746
0.8268	Intermediate Similarity	NPC35924
0.8266	Intermediate Similarity	NPC89809
0.8266	Intermediate Similarity	NPC473278
0.8266	Intermediate Similarity	NPC260504
0.8256	Intermediate Similarity	NPC471286
0.8256	Intermediate Similarity	NPC91288
0.8249	Intermediate Similarity	NPC67629
0.8249	Intermediate Similarity	NPC79736
0.8246	Intermediate Similarity	NPC92589
0.8246	Intermediate Similarity	NPC186228
0.8246	Intermediate Similarity	NPC100465
0.8246	Intermediate Similarity	NPC195685
0.8246	Intermediate Similarity	NPC210961
0.8246	Intermediate Similarity	NPC115624
0.8246	Intermediate Similarity	NPC477628
0.8246	Intermediate Similarity	NPC270675
0.8246	Intermediate Similarity	NPC152424
0.8246	Intermediate Similarity	NPC472994
0.8246	Intermediate Similarity	NPC101636
0.8246	Intermediate Similarity	NPC477629
0.8242	Intermediate Similarity	NPC96599
0.8239	Intermediate Similarity	NPC172033
0.8239	Intermediate Similarity	NPC88560
0.8239	Intermediate Similarity	NPC316539
0.8239	Intermediate Similarity	NPC175230
0.8235	Intermediate Similarity	NPC73511
0.8235	Intermediate Similarity	NPC173726
0.8235	Intermediate Similarity	NPC50430
0.8235	Intermediate Similarity	NPC241600
0.8235	Intermediate Similarity	NPC169605
0.8229	Intermediate Similarity	NPC188815
0.8229	Intermediate Similarity	NPC469344
0.8225	Intermediate Similarity	NPC165483
0.8225	Intermediate Similarity	NPC149368
0.8225	Intermediate Similarity	NPC206378
0.8225	Intermediate Similarity	NPC45165
0.8225	Intermediate Similarity	NPC265480
0.8225	Intermediate Similarity	NPC478055
0.8218	Intermediate Similarity	NPC208818
0.8218	Intermediate Similarity	NPC471860
0.8218	Intermediate Similarity	NPC471859
0.8214	Intermediate Similarity	NPC106625
0.8208	Intermediate Similarity	NPC139060
0.8204	Intermediate Similarity	NPC56184
0.8202	Intermediate Similarity	NPC241196
0.8202	Intermediate Similarity	NPC267549
0.8199	Intermediate Similarity	NPC108674
0.8198	Intermediate Similarity	NPC476244
0.8198	Intermediate Similarity	NPC150164
0.8198	Intermediate Similarity	NPC298171
0.8198	Intermediate Similarity	NPC326278
0.8198	Intermediate Similarity	NPC27942
0.8193	Intermediate Similarity	NPC229882
0.8193	Intermediate Similarity	NPC100818
0.8193	Intermediate Similarity	NPC35097
0.8193	Intermediate Similarity	NPC158635
0.8187	Intermediate Similarity	NPC142860
0.8187	Intermediate Similarity	NPC246469
0.8187	Intermediate Similarity	NPC271270
0.8187	Intermediate Similarity	NPC97285
0.8187	Intermediate Similarity	NPC473623
0.8182	Intermediate Similarity	NPC217822
0.8182	Intermediate Similarity	NPC9002
0.8182	Intermediate Similarity	NPC221288
0.8182	Intermediate Similarity	NPC137871
0.8182	Intermediate Similarity	NPC101399
0.8182	Intermediate Similarity	NPC11847
0.8182	Intermediate Similarity	NPC257011
0.8182	Intermediate Similarity	NPC474522
0.8182	Intermediate Similarity	NPC235698
0.8182	Intermediate Similarity	NPC261254
0.8182	Intermediate Similarity	NPC288152
0.8176	Intermediate Similarity	NPC197896
0.8176	Intermediate Similarity	NPC6985
0.8176	Intermediate Similarity	NPC161749
0.8176	Intermediate Similarity	NPC313163
0.8176	Intermediate Similarity	NPC258035
0.8176	Intermediate Similarity	NPC156457
0.8171	Intermediate Similarity	NPC21956
0.8167	Intermediate Similarity	NPC475662
0.8167	Intermediate Similarity	NPC293227
0.8167	Intermediate Similarity	NPC473717
0.8167	Intermediate Similarity	NPC473631
0.8166	Intermediate Similarity	NPC39351
0.8166	Intermediate Similarity	NPC72649
0.8166	Intermediate Similarity	NPC99233
0.8166	Intermediate Similarity	NPC169248
0.8166	Intermediate Similarity	NPC186316
0.8166	Intermediate Similarity	NPC97052
0.8166	Intermediate Similarity	NPC95090
0.8166	Intermediate Similarity	NPC27408
0.8166	Intermediate Similarity	NPC26195
0.8161	Intermediate Similarity	NPC306475
0.8161	Intermediate Similarity	NPC68592
0.8161	Intermediate Similarity	NPC262222
0.8161	Intermediate Similarity	NPC298666
0.8155	Intermediate Similarity	NPC299706
0.8155	Intermediate Similarity	NPC61604
0.8155	Intermediate Similarity	NPC115466
0.8155	Intermediate Similarity	NPC259182
0.8155	Intermediate Similarity	NPC245615
0.8155	Intermediate Similarity	NPC121001
0.815	Intermediate Similarity	NPC183672
0.815	Intermediate Similarity	NPC473644
0.815	Intermediate Similarity	NPC257566
0.815	Intermediate Similarity	NPC80068
0.815	Intermediate Similarity	NPC116759
0.815	Intermediate Similarity	NPC124155
0.815	Intermediate Similarity	NPC14294
0.815	Intermediate Similarity	NPC121703
0.8148	Intermediate Similarity	NPC472353
0.8148	Intermediate Similarity	NPC307287
0.8146	Intermediate Similarity	NPC475233
0.8146	Intermediate Similarity	NPC325176
0.8142	Intermediate Similarity	NPC230670
0.8142	Intermediate Similarity	NPC71385
0.814	Intermediate Similarity	NPC259957
0.814	Intermediate Similarity	NPC129217
0.814	Intermediate Similarity	NPC48093
0.814	Intermediate Similarity	NPC282169
0.814	Intermediate Similarity	NPC216496
0.814	Intermediate Similarity	NPC85707
0.814	Intermediate Similarity	NPC303913
0.814	Intermediate Similarity	NPC224530
0.814	Intermediate Similarity	NPC159579
0.8129	Intermediate Similarity	NPC138811
0.8129	Intermediate Similarity	NPC279732
0.8129	Intermediate Similarity	NPC473634
0.8129	Intermediate Similarity	NPC22062
0.8129	Intermediate Similarity	NPC470607
0.8125	Intermediate Similarity	NPC199079
0.8125	Intermediate Similarity	NPC277532
0.8125	Intermediate Similarity	NPC8704
0.8125	Intermediate Similarity	NPC472159
0.8125	Intermediate Similarity	NPC175429
0.8125	Intermediate Similarity	NPC209550
0.8125	Intermediate Similarity	NPC287884
0.8125	Intermediate Similarity	NPC218161
0.8125	Intermediate Similarity	NPC149011
0.8125	Intermediate Similarity	NPC96605
0.8125	Intermediate Similarity	NPC212748
0.8125	Intermediate Similarity	NPC470712

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 NPC254071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	806
0.2-0.3	1822
0.3-0.4	2618
0.4-0.5	2130
0.5-0.6	1021
0.6-0.7	343
0.7-0.8	102
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7199	Phase 2
0.8363	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD7685	Pre-registration
0.8114	Intermediate Similarity	NPD7228	Approved
0.8107	Intermediate Similarity	NPD8455	Phase 2
0.8068	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4965	Approved
0.8012	Intermediate Similarity	NPD4967	Phase 2
0.8012	Intermediate Similarity	NPD4966	Approved
0.7941	Intermediate Similarity	NPD37	Approved
0.7921	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.791	Intermediate Similarity	NPD3818	Discontinued
0.7865	Intermediate Similarity	NPD7054	Approved
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD6559	Discontinued
0.7833	Intermediate Similarity	NPD7240	Approved
0.7821	Intermediate Similarity	NPD7472	Approved
0.7803	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7808	Phase 3
0.779	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7075	Discontinued
0.7738	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7251	Discontinued
0.7688	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3787	Discontinued
0.768	Intermediate Similarity	NPD6797	Phase 2
0.7674	Intermediate Similarity	NPD7411	Suspended
0.765	Intermediate Similarity	NPD8313	Approved
0.765	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6005	Phase 3
0.7636	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6002	Phase 3
0.7636	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6004	Phase 3
0.7622	Intermediate Similarity	NPD7033	Discontinued
0.7616	Intermediate Similarity	NPD4380	Phase 2
0.7598	Intermediate Similarity	NPD6166	Phase 2
0.7598	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7819	Suspended
0.7557	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD6355	Discontinued
0.7529	Intermediate Similarity	NPD6801	Discontinued
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7486	Intermediate Similarity	NPD7229	Phase 3
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5844	Phase 1
0.7471	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7097	Phase 1
0.7453	Intermediate Similarity	NPD4908	Phase 1
0.7436	Intermediate Similarity	NPD7680	Approved
0.7429	Intermediate Similarity	NPD1934	Approved
0.7386	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5760	Phase 2
0.7386	Intermediate Similarity	NPD5761	Phase 2
0.7374	Intermediate Similarity	NPD5494	Approved
0.7371	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6799	Approved
0.7363	Intermediate Similarity	NPD7473	Discontinued
0.7362	Intermediate Similarity	NPD6798	Discontinued
0.7362	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7783	Phase 2
0.735	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5402	Approved
0.7345	Intermediate Similarity	NPD3817	Phase 2
0.7341	Intermediate Similarity	NPD5403	Approved
0.7341	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5647	Approved
0.7326	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7799	Discontinued
0.7321	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6599	Discontinued
0.7294	Intermediate Similarity	NPD4628	Phase 3
0.7293	Intermediate Similarity	NPD6232	Discontinued
0.7289	Intermediate Similarity	NPD6653	Approved
0.7278	Intermediate Similarity	NPD1549	Phase 2
0.725	Intermediate Similarity	NPD8151	Discontinued
0.7249	Intermediate Similarity	NPD8434	Phase 2
0.7238	Intermediate Similarity	NPD8127	Discontinued
0.7238	Intermediate Similarity	NPD6959	Discontinued
0.7225	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5401	Approved
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7212	Intermediate Similarity	NPD6233	Phase 2
0.7207	Intermediate Similarity	NPD3882	Suspended
0.72	Intermediate Similarity	NPD1653	Approved
0.7191	Intermediate Similarity	NPD2801	Approved
0.7172	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD2796	Approved
0.7159	Intermediate Similarity	NPD7458	Discontinued
0.7157	Intermediate Similarity	NPD7930	Approved
0.7135	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5124	Phase 1
0.7125	Intermediate Similarity	NPD1091	Approved
0.7095	Intermediate Similarity	NPD1465	Phase 2
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3750	Approved
0.7083	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1613	Approved
0.7065	Intermediate Similarity	NPD7583	Approved
0.7065	Intermediate Similarity	NPD7584	Approved
0.7053	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7870	Phase 2
0.705	Intermediate Similarity	NPD7871	Phase 2
0.7044	Intermediate Similarity	NPD7874	Approved
0.7044	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6674	Discontinued
0.703	Intermediate Similarity	NPD7585	Approved
0.7029	Intermediate Similarity	NPD2532	Approved
0.7029	Intermediate Similarity	NPD2533	Approved
0.7029	Intermediate Similarity	NPD2534	Approved
0.702	Intermediate Similarity	NPD6780	Approved
0.702	Intermediate Similarity	NPD6782	Approved
0.702	Intermediate Similarity	NPD6781	Approved
0.702	Intermediate Similarity	NPD6777	Approved
0.702	Intermediate Similarity	NPD6776	Approved
0.702	Intermediate Similarity	NPD6779	Approved
0.702	Intermediate Similarity	NPD6778	Approved
0.7019	Intermediate Similarity	NPD1610	Phase 2
0.7018	Intermediate Similarity	NPD7266	Discontinued
0.7	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD7696	Phase 3
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD7698	Approved
0.6994	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6273	Approved
0.6977	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1511	Approved
0.697	Remote Similarity	NPD2861	Phase 2
0.6965	Remote Similarity	NPD8319	Approved
0.6965	Remote Similarity	NPD8320	Phase 1
0.6964	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6190	Approved
0.6951	Remote Similarity	NPD6362	Approved
0.6951	Remote Similarity	NPD2797	Approved
0.6949	Remote Similarity	NPD920	Approved
0.6946	Remote Similarity	NPD7701	Phase 2
0.6946	Remote Similarity	NPD3268	Approved
0.6936	Remote Similarity	NPD1652	Phase 2
0.6927	Remote Similarity	NPD7801	Approved
0.6927	Remote Similarity	NPD7028	Phase 2
0.6923	Remote Similarity	NPD5735	Approved
0.6914	Remote Similarity	NPD5058	Phase 3
0.6901	Remote Similarity	NPD3748	Approved
0.6893	Remote Similarity	NPD1512	Approved
0.6891	Remote Similarity	NPD8150	Discontinued
0.6886	Remote Similarity	NPD7095	Approved
0.6872	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1608	Approved
0.6866	Remote Similarity	NPD6823	Phase 2
0.6864	Remote Similarity	NPD4140	Approved
0.6864	Remote Similarity	NPD1240	Approved
0.686	Remote Similarity	NPD1551	Phase 2
0.6839	Remote Similarity	NPD2800	Approved
0.6836	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7700	Phase 2
0.6834	Remote Similarity	NPD7699	Phase 2
0.6832	Remote Similarity	NPD7497	Discontinued
0.6826	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2799	Discontinued
0.68	Remote Similarity	NPD7466	Approved
0.6792	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3926	Phase 2
0.6786	Remote Similarity	NPD3027	Phase 3
0.6784	Remote Similarity	NPD1607	Approved
0.6782	Remote Similarity	NPD2424	Discontinued
0.6782	Remote Similarity	NPD5958	Discontinued
0.6778	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3226	Approved
0.6771	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6534	Approved
0.6768	Remote Similarity	NPD6535	Approved
0.6766	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7999	Approved
0.6765	Remote Similarity	NPD4060	Phase 1
0.6754	Remote Similarity	NPD5953	Discontinued
0.6746	Remote Similarity	NPD3764	Approved
0.6746	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD1243	Approved
0.6738	Remote Similarity	NPD7315	Approved
0.6737	Remote Similarity	NPD7286	Phase 2
0.6735	Remote Similarity	NPD4287	Approved
0.6726	Remote Similarity	NPD6832	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