NPASS Compound

Structure

CID49451 OpenBabel06191715382D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.3652 -3.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7130 -0.5067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7981 0.5189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9527 -2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1361 -2.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -0.9262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3506 -2.5233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 -2.1818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9422 -1.4624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4765 -2.1999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2092 -0.4440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7484 -1.3988 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1151 -1.1390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2749 -0.9262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3296 -1.1208 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2754 0.0629 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6742 -2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7276 -1.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9739 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4870 -1.4987 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7782 -0.9628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1355 -0.1431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6674 -1.0761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3005 0.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0668 0.9747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4994 -2.5809 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 1.1082 -2.4202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 8 18 1 1 0 0 0 9 15 1 0 0 0 0 9 21 2 0 0 0 0 10 20 1 6 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 11 22 1 1 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 12 23 1 1 0 0 0 13 18 1 1 0 0 0 13 20 1 0 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 18 1 1 0 0 0 15 24 1 0 0 0 0 16 19 1 6 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 17 28 1 0 0 0 0 18 2 1 1 0 0 0 19 3 1 1 0 0 0 19 27 1 0 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.16
Volume:	374.106
LogP:	0.366
LogD:	-0.084
LogS:	-3.909
# Rotatable Bonds:	0
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	6.573
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.304
MDCK Permeability:	7.701853610342368e-05
Pgp-inhibitor:	0.714
Pgp-substrate:	0.75
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.506
Plasma Protein Binding (PPB):	35.91682815551758%
Volume Distribution (VD):	0.354
Pgp-substrate:	56.9699592590332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.793
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	4.022
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.513
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.138
Carcinogencity:	0.124
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.538

Download Data

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

Natural Product: NPC49451

Natural Product ID:	NPC49451
*Common Name:**	Yadanziolide C
IUPAC Name:	n.a.
Synonyms:	Samaderine Z; Yadanziolide C
Standard InCHIKey:	KDVYRSSTPWSAJC-GGUABDNCSA-N
Standard InCHI:	InChI=1S/C20H26O8/c1-7-4-9(21)15(24)18(2)8(7)5-10-20-6-27-19(3,16(25)11(22)13(18)20)14(20)12(23)17(26)28-10/h4,8,10-16,22-25H,5-6H2,1-3H3/t8-,10+,11+,12+,13+,14-,15+,16-,18-,19-,20+/m0/s1
SMILES:	O=C1O[C@@H]2C[C@H]3C(=CC(=O)[C@H]([C@@]3([C@@H]3[C@@]42[C@@H]([C@H]1O)[C@](C)(OC4)[C@H]([C@@H]3O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469501
PubChem CID:	44593590
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO22346	Simaba cedron	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644063]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3635	Omphalotus olearius	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6551	Lythrum lanceolatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11902	Gomphocarpus fruticosus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4438	Austrobrickellia patens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1129	Punctularia atropurpurascens	Species	Punctulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2230	Fusarium sporotrichiella	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27970	Desmonostoc muscorum	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10692	Euryops othonnoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22346	Simaba cedron	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11660	Qualea paraensis	Species	Vochysiaceae	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
EC50	1
IC50	3
Others	1

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1500.0	nM	PMID[458210]
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	10000.0	nM	PMID[458210]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[458210]
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	>	6.7	n.a.	PMID[458210]
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.4	ug.mL-1	PMID[458211]

☑ 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 NPC49451 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	241
0.1-0.2	1375
0.2-0.3	4318
0.3-0.4	7637
0.4-0.5	12266
0.5-0.6	6920
0.6-0.7	5340
0.7-0.8	3908
0.8-0.85	531
0.85-0.9	78
0.9-0.95	64
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9811	High Similarity	NPC328374
0.9811	High Similarity	NPC96312
0.9811	High Similarity	NPC251236
0.9811	High Similarity	NPC40632
0.972	High Similarity	NPC97908
0.972	High Similarity	NPC470854
0.972	High Similarity	NPC122033
0.972	High Similarity	NPC287343
0.972	High Similarity	NPC474654
0.9717	High Similarity	NPC473798
0.963	High Similarity	NPC17772
0.9528	High Similarity	NPC289312
0.9528	High Similarity	NPC11252
0.9528	High Similarity	NPC474516
0.9519	High Similarity	NPC293850
0.945	High Similarity	NPC188667
0.945	High Similarity	NPC204552
0.9444	High Similarity	NPC152199
0.9444	High Similarity	NPC134869
0.9444	High Similarity	NPC235539
0.9439	High Similarity	NPC7921
0.9439	High Similarity	NPC208998
0.9434	High Similarity	NPC201992
0.9423	High Similarity	NPC3316
0.9423	High Similarity	NPC144854
0.9369	High Similarity	NPC102822
0.9369	High Similarity	NPC477046
0.9364	High Similarity	NPC470777
0.9352	High Similarity	NPC474906
0.9352	High Similarity	NPC18547
0.9333	High Similarity	NPC192813
0.9333	High Similarity	NPC277017
0.9333	High Similarity	NPC154608
0.9279	High Similarity	NPC112038
0.9273	High Similarity	NPC251310
0.9273	High Similarity	NPC297179
0.9266	High Similarity	NPC474734
0.9266	High Similarity	NPC207217
0.9259	High Similarity	NPC51978
0.9252	High Similarity	NPC146945
0.9252	High Similarity	NPC171888
0.9189	High Similarity	NPC469488
0.9182	High Similarity	NPC176513
0.9182	High Similarity	NPC473590
0.9182	High Similarity	NPC470775
0.9174	High Similarity	NPC323821
0.9174	High Similarity	NPC143268
0.9174	High Similarity	NPC45218
0.9174	High Similarity	NPC268238
0.9143	High Similarity	NPC102352
0.9123	High Similarity	NPC24651
0.9115	High Similarity	NPC312833
0.9099	High Similarity	NPC470776
0.9091	High Similarity	NPC16081
0.9091	High Similarity	NPC173686
0.9035	High Similarity	NPC91693
0.9035	High Similarity	NPC18945
0.9035	High Similarity	NPC67251
0.9035	High Similarity	NPC105926
0.9035	High Similarity	NPC265557
0.9018	High Similarity	NPC475775
0.9018	High Similarity	NPC476529
0.8991	High Similarity	NPC302146
0.8991	High Similarity	NPC472002
0.8981	High Similarity	NPC210005
0.8962	High Similarity	NPC181357
0.8957	High Similarity	NPC476729
0.8938	High Similarity	NPC109607
0.8938	High Similarity	NPC107338
0.8919	High Similarity	NPC259306
0.8919	High Similarity	NPC179626
0.8919	High Similarity	NPC470628
0.8919	High Similarity	NPC474046
0.8909	High Similarity	NPC194100
0.8889	High Similarity	NPC141350
0.8868	High Similarity	NPC65523
0.886	High Similarity	NPC470779
0.8839	High Similarity	NPC309433
0.8829	High Similarity	NPC470919
0.8829	High Similarity	NPC469877
0.8793	High Similarity	NPC470922
0.8783	High Similarity	NPC222688
0.8774	High Similarity	NPC275583
0.8716	High Similarity	NPC310546
0.8716	High Similarity	NPC143706
0.8716	High Similarity	NPC27814
0.8716	High Similarity	NPC472534
0.8707	High Similarity	NPC227397
0.8704	High Similarity	NPC230541
0.8673	High Similarity	NPC473968
0.8667	High Similarity	NPC472972
0.8661	High Similarity	NPC117712
0.8661	High Similarity	NPC243354
0.8649	High Similarity	NPC90769
0.8649	High Similarity	NPC280782
0.8644	High Similarity	NPC476008
0.8632	High Similarity	NPC473255
0.8624	High Similarity	NPC94942
0.8571	High Similarity	NPC194273
0.8571	High Similarity	NPC188291
0.8571	High Similarity	NPC198539
0.8559	High Similarity	NPC469656
0.8559	High Similarity	NPC477745
0.8559	High Similarity	NPC471243
0.8559	High Similarity	NPC474846
0.8559	High Similarity	NPC469655
0.8559	High Similarity	NPC188738
0.8534	High Similarity	NPC275675
0.8532	High Similarity	NPC59530
0.8519	High Similarity	NPC475036
0.8512	High Similarity	NPC100390
0.8512	High Similarity	NPC254614
0.8509	High Similarity	NPC146432
0.8509	High Similarity	NPC470778
0.8496	Intermediate Similarity	NPC247069
0.8496	Intermediate Similarity	NPC299849
0.8487	Intermediate Similarity	NPC470780
0.8487	Intermediate Similarity	NPC470882
0.8468	Intermediate Similarity	NPC5103
0.8468	Intermediate Similarity	NPC474567
0.8468	Intermediate Similarity	NPC253906
0.8462	Intermediate Similarity	NPC65858
0.8448	Intermediate Similarity	NPC109973
0.8448	Intermediate Similarity	NPC471406
0.844	Intermediate Similarity	NPC477877
0.8421	Intermediate Similarity	NPC89929
0.8421	Intermediate Similarity	NPC213084
0.8421	Intermediate Similarity	NPC190185
0.8421	Intermediate Similarity	NPC266728
0.8421	Intermediate Similarity	NPC49492
0.8417	Intermediate Similarity	NPC475636
0.8417	Intermediate Similarity	NPC295220
0.8407	Intermediate Similarity	NPC94509
0.8407	Intermediate Similarity	NPC320118
0.8407	Intermediate Similarity	NPC477266
0.8407	Intermediate Similarity	NPC471204
0.8407	Intermediate Similarity	NPC25909
0.8407	Intermediate Similarity	NPC962
0.8407	Intermediate Similarity	NPC255017
0.8407	Intermediate Similarity	NPC250109
0.8403	Intermediate Similarity	NPC285091
0.8403	Intermediate Similarity	NPC87662
0.8403	Intermediate Similarity	NPC181999
0.8403	Intermediate Similarity	NPC225049
0.8393	Intermediate Similarity	NPC157476
0.839	Intermediate Similarity	NPC135038
0.839	Intermediate Similarity	NPC43252
0.8381	Intermediate Similarity	NPC256227
0.8378	Intermediate Similarity	NPC41405
0.8376	Intermediate Similarity	NPC470921
0.8364	Intermediate Similarity	NPC202524
0.8364	Intermediate Similarity	NPC293512
0.8362	Intermediate Similarity	NPC127530
0.8362	Intermediate Similarity	NPC475041
0.8362	Intermediate Similarity	NPC473920
0.8362	Intermediate Similarity	NPC279143
0.8361	Intermediate Similarity	NPC6274
0.8361	Intermediate Similarity	NPC102316
0.8361	Intermediate Similarity	NPC33378
0.8361	Intermediate Similarity	NPC471855
0.8361	Intermediate Similarity	NPC254146
0.8349	Intermediate Similarity	NPC258532
0.8349	Intermediate Similarity	NPC301787
0.8349	Intermediate Similarity	NPC471293
0.8348	Intermediate Similarity	NPC27999
0.8348	Intermediate Similarity	NPC53396
0.8348	Intermediate Similarity	NPC98249
0.8348	Intermediate Similarity	NPC477116
0.8348	Intermediate Similarity	NPC58662
0.8348	Intermediate Similarity	NPC469684
0.8348	Intermediate Similarity	NPC13713
0.8347	Intermediate Similarity	NPC54614
0.8347	Intermediate Similarity	NPC309096
0.8347	Intermediate Similarity	NPC264192
0.8333	Intermediate Similarity	NPC473265
0.8333	Intermediate Similarity	NPC475633
0.8333	Intermediate Similarity	NPC102088
0.832	Intermediate Similarity	NPC596
0.8319	Intermediate Similarity	NPC234042
0.8319	Intermediate Similarity	NPC269530
0.8319	Intermediate Similarity	NPC152117
0.8306	Intermediate Similarity	NPC262813
0.8305	Intermediate Similarity	NPC269642
0.8305	Intermediate Similarity	NPC471965
0.8304	Intermediate Similarity	NPC85391
0.8304	Intermediate Similarity	NPC100908
0.8304	Intermediate Similarity	NPC5284
0.8293	Intermediate Similarity	NPC168879
0.8291	Intermediate Similarity	NPC478051
0.8291	Intermediate Similarity	NPC476961
0.8288	Intermediate Similarity	NPC273155
0.8288	Intermediate Similarity	NPC275539
0.8288	Intermediate Similarity	NPC189075
0.8288	Intermediate Similarity	NPC476479
0.8288	Intermediate Similarity	NPC19412
0.8276	Intermediate Similarity	NPC284707
0.8276	Intermediate Similarity	NPC106644
0.8273	Intermediate Similarity	NPC222833
0.8261	Intermediate Similarity	NPC478216
0.8257	Intermediate Similarity	NPC474575

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 NPC49451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1631
0.2-0.3	3810
0.3-0.4	2213
0.4-0.5	742
0.5-0.6	261
0.6-0.7	125
0.7-0.8	142
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
0.8291	Intermediate Similarity	NPD6319	Approved
0.8246	Intermediate Similarity	NPD4632	Approved
0.8235	Intermediate Similarity	NPD8328	Phase 3
0.8214	Intermediate Similarity	NPD6372	Approved
0.8214	Intermediate Similarity	NPD6373	Approved
0.8158	Intermediate Similarity	NPD8297	Approved
0.8125	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6402	Approved
0.8108	Intermediate Similarity	NPD7128	Approved
0.8108	Intermediate Similarity	NPD5739	Approved
0.8108	Intermediate Similarity	NPD6675	Approved
0.807	Intermediate Similarity	NPD6649	Approved
0.807	Intermediate Similarity	NPD6650	Approved
0.8036	Intermediate Similarity	NPD5697	Approved
0.8036	Intermediate Similarity	NPD5701	Approved
0.7965	Intermediate Similarity	NPD7320	Approved
0.7965	Intermediate Similarity	NPD6899	Approved
0.7965	Intermediate Similarity	NPD6881	Approved
0.7946	Intermediate Similarity	NPD6008	Approved
0.7895	Intermediate Similarity	NPD6013	Approved
0.7895	Intermediate Similarity	NPD6012	Approved
0.7895	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6014	Approved
0.7895	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6009	Approved
0.7881	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7492	Approved
0.7845	Intermediate Similarity	NPD6882	Approved
0.7833	Intermediate Similarity	NPD6059	Approved
0.7833	Intermediate Similarity	NPD6054	Approved
0.7826	Intermediate Similarity	NPD7102	Approved
0.7826	Intermediate Similarity	NPD6883	Approved
0.7826	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7290	Approved
0.7823	Intermediate Similarity	NPD7736	Approved
0.7807	Intermediate Similarity	NPD6011	Approved
0.7805	Intermediate Similarity	NPD6616	Approved
0.7798	Intermediate Similarity	NPD4755	Approved
0.7769	Intermediate Similarity	NPD5983	Phase 2
0.7769	Intermediate Similarity	NPD6016	Approved
0.7769	Intermediate Similarity	NPD6015	Approved
0.7759	Intermediate Similarity	NPD6869	Approved
0.7759	Intermediate Similarity	NPD6617	Approved
0.7759	Intermediate Similarity	NPD6847	Approved
0.7759	Intermediate Similarity	NPD8130	Phase 1
0.7742	Intermediate Similarity	NPD7078	Approved
0.7742	Intermediate Similarity	NPD8293	Discontinued
0.7719	Intermediate Similarity	NPD6412	Phase 2
0.7705	Intermediate Similarity	NPD6370	Approved
0.7705	Intermediate Similarity	NPD5988	Approved
0.7672	Intermediate Similarity	NPD4634	Approved
0.7661	Intermediate Similarity	NPD7507	Approved
0.7658	Intermediate Similarity	NPD5285	Approved
0.7658	Intermediate Similarity	NPD5286	Approved
0.7658	Intermediate Similarity	NPD4700	Approved
0.7658	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD7604	Phase 2
0.7636	Intermediate Similarity	NPD7902	Approved
0.7619	Intermediate Similarity	NPD7319	Approved
0.7607	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7565	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4697	Phase 3
0.7523	Intermediate Similarity	NPD7748	Approved
0.7522	Intermediate Similarity	NPD5224	Approved
0.7522	Intermediate Similarity	NPD5211	Phase 2
0.7522	Intermediate Similarity	NPD5225	Approved
0.7522	Intermediate Similarity	NPD5226	Approved
0.7522	Intermediate Similarity	NPD4633	Approved
0.752	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.748	Intermediate Similarity	NPD6921	Approved
0.7478	Intermediate Similarity	NPD4768	Approved
0.7478	Intermediate Similarity	NPD4767	Approved
0.7477	Intermediate Similarity	NPD6083	Phase 2
0.7477	Intermediate Similarity	NPD6084	Phase 2
0.7456	Intermediate Similarity	NPD5175	Approved
0.7456	Intermediate Similarity	NPD5174	Approved
0.7453	Intermediate Similarity	NPD3573	Approved
0.7434	Intermediate Similarity	NPD5223	Approved
0.7431	Intermediate Similarity	NPD6399	Phase 3
0.7411	Intermediate Similarity	NPD5696	Approved
0.7411	Intermediate Similarity	NPD4225	Approved
0.7391	Intermediate Similarity	NPD5141	Approved
0.7387	Intermediate Similarity	NPD5221	Approved
0.7387	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5222	Approved
0.7364	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7900	Approved
0.7358	Intermediate Similarity	NPD3618	Phase 1
0.735	Intermediate Similarity	NPD4729	Approved
0.735	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5173	Approved
0.7317	Intermediate Similarity	NPD7100	Approved
0.7317	Intermediate Similarity	NPD7101	Approved
0.7317	Intermediate Similarity	NPD7516	Approved
0.7315	Intermediate Similarity	NPD5328	Approved
0.7304	Intermediate Similarity	NPD4754	Approved
0.7297	Intermediate Similarity	NPD5695	Phase 3
0.7295	Intermediate Similarity	NPD6317	Approved
0.7266	Intermediate Similarity	NPD6033	Approved
0.7257	Intermediate Similarity	NPD7638	Approved
0.7236	Intermediate Similarity	NPD6314	Approved
0.7236	Intermediate Similarity	NPD6335	Approved
0.7236	Intermediate Similarity	NPD7327	Approved
0.7236	Intermediate Similarity	NPD6313	Approved
0.7236	Intermediate Similarity	NPD7328	Approved
0.7227	Intermediate Similarity	NPD5250	Approved
0.7227	Intermediate Similarity	NPD5248	Approved
0.7227	Intermediate Similarity	NPD5247	Approved
0.7227	Intermediate Similarity	NPD5249	Phase 3
0.7227	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5282	Discontinued
0.7203	Intermediate Similarity	NPD5128	Approved
0.72	Intermediate Similarity	NPD6909	Approved
0.72	Intermediate Similarity	NPD8513	Phase 3
0.72	Intermediate Similarity	NPD8516	Approved
0.72	Intermediate Similarity	NPD6908	Approved
0.72	Intermediate Similarity	NPD8515	Approved
0.72	Intermediate Similarity	NPD8517	Approved
0.7193	Intermediate Similarity	NPD7640	Approved
0.7193	Intermediate Similarity	NPD7639	Approved
0.7182	Intermediate Similarity	NPD6079	Approved
0.7156	Intermediate Similarity	NPD4753	Phase 2
0.7117	Intermediate Similarity	NPD4202	Approved
0.7073	Intermediate Similarity	NPD6868	Approved
0.7064	Intermediate Similarity	NPD5737	Approved
0.7064	Intermediate Similarity	NPD6672	Approved
0.7063	Intermediate Similarity	NPD8380	Approved
0.7063	Intermediate Similarity	NPD8335	Approved
0.7063	Intermediate Similarity	NPD8378	Approved
0.7063	Intermediate Similarity	NPD8379	Approved
0.7063	Intermediate Similarity	NPD8296	Approved
0.7063	Intermediate Similarity	NPD8033	Approved
0.7049	Intermediate Similarity	NPD8133	Approved
0.7027	Intermediate Similarity	NPD6411	Approved
0.7025	Intermediate Similarity	NPD5217	Approved
0.7025	Intermediate Similarity	NPD5215	Approved
0.7025	Intermediate Similarity	NPD5216	Approved
0.7025	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5210	Approved
0.6991	Remote Similarity	NPD4629	Approved
0.6991	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8377	Approved
0.6984	Remote Similarity	NPD8294	Approved
0.6981	Remote Similarity	NPD3667	Approved
0.697	Remote Similarity	NPD7260	Phase 2
0.6942	Remote Similarity	NPD5169	Approved
0.6942	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5135	Approved
0.6937	Remote Similarity	NPD46	Approved
0.6937	Remote Similarity	NPD6698	Approved
0.6929	Remote Similarity	NPD7503	Approved
0.6909	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5127	Approved
0.6881	Remote Similarity	NPD6684	Approved
0.6881	Remote Similarity	NPD7521	Approved
0.6881	Remote Similarity	NPD5330	Approved
0.6881	Remote Similarity	NPD7146	Approved
0.6881	Remote Similarity	NPD6409	Approved
0.6881	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD8035	Phase 2
0.6852	Remote Similarity	NPD3665	Phase 1
0.6852	Remote Similarity	NPD4786	Approved
0.6852	Remote Similarity	NPD3666	Approved
0.6852	Remote Similarity	NPD3133	Approved
0.6847	Remote Similarity	NPD6673	Approved
0.6847	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6904	Approved
0.6847	Remote Similarity	NPD6080	Approved
0.6847	Remote Similarity	NPD6101	Approved
0.6847	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5344	Discontinued
0.6833	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6053	Discontinued
0.6822	Remote Similarity	NPD6067	Discontinued
0.6794	Remote Similarity	NPD8074	Phase 3
0.6792	Remote Similarity	NPD4695	Discontinued
0.6791	Remote Similarity	NPD6845	Suspended
0.6777	Remote Similarity	NPD5168	Approved
0.6757	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD6001	Approved
0.6727	Remote Similarity	NPD5279	Phase 3
0.6727	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5284	Approved
0.6726	Remote Similarity	NPD5281	Approved
0.6726	Remote Similarity	NPD5693	Phase 1
0.672	Remote Similarity	NPD5167	Approved
0.6697	Remote Similarity	NPD4197	Approved
0.6696	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6642	Remote Similarity	NPD5956	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6637	Remote Similarity	NPD5692	Phase 3

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