NPASS Compound

Structure

NPC473423 OpenBabel07101718182D 44 47 0 0 1 0 0 0 0 0999 V2000 -0.5924 1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -2.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4397 -2.9401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4187 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5603 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8642 -0.5104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5222 -1.4501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2470 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3809 -2.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2470 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 -2.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3809 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6489 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7829 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 0.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1736 -0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5924 -1.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4397 -2.9401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5209 2.2704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0603 1.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 -1.3268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -0.6840 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9168 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7057 0.3008 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.6840 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4397 -1.2080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1133 0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4397 0.5240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8794 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0603 -3.8061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6946 3.2552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5603 2.2561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9397 0.3420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9168 0.3160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 -2.0741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2870 1.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 1.3900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0508 -1.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 34 1 0 0 0 0 7 34 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 35 1 0 0 0 0 18 26 1 0 0 0 0 19 1 1 6 0 0 0 19 26 1 0 0 0 0 19 29 1 0 0 0 0 20 27 1 0 0 0 0 20 30 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 38 2 0 0 0 0 23 43 1 0 0 0 0 25 18 1 6 0 0 0 25 31 1 0 0 0 0 25 34 1 0 0 0 0 26 39 2 0 0 0 0 27 44 1 6 0 0 0 28 40 2 0 0 0 0 28 44 1 0 0 0 0 29 32 1 0 0 0 0 29 34 1 0 0 0 0 30 31 1 0 0 0 0 30 35 1 0 0 0 0 31 41 1 6 0 0 0 32 33 1 0 0 0 0 32 42 1 1 0 0 0 33 35 1 6 0 0 0 33 43 1 0 0 0 0 35 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.3
Volume:	632.438
LogP:	4.071
LogD:	2.772
LogS:	-5.093
# Rotatable Bonds:	10
TPSA:	122.27
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	5.626
Fsp3:	0.571
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:	-4.96
MDCK Permeability:	6.989961548242718e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	79.92804718017578%
Volume Distribution (VD):	1.7
Pgp-substrate:	14.193865776062012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.276
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.541
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.855
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	3.135
Half-life (T1/2):	0.041

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.991
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.661
Skin Sensitization:	0.067
Carcinogencity:	0.023
Eye Corrosion:	0.005
Eye Irritation:	0.011
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC473423

Natural Product ID:	NPC473423
*Common Name:**	OLBKUXNDAXKWQK-TYDIEVEDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OLBKUXNDAXKWQK-TYDIEVEDSA-N
Standard InCHI:	InChI=1S/C35H44O9/c1-19-26(39)18-25-31(41-21(3)36)30-20(2)27(44-28(40)15-14-24-12-10-9-11-13-24)16-17-35(30,8)33(43-23(5)38)32(42-22(4)37)29(19)34(25,6)7/h9-15,19,25,27,29-33H,2,16-18H2,1,3-8H3/b15-14+/t19-,25+,27+,29?,30?,31-,32-,33+,35-/m1/s1
SMILES:	CC1C2C(C(C3(CCC(C(=C)C3C(C(C2(C)C)CC1=O)OC(=O)C)OC(=O)C=CC4=CC=CC=C4)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL42798
PubChem CID:	44286763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO33211	japanese yew	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9873389]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	8

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	5.8	ug.mL-1	PMID[492927]
NPT2	Others	Unspecified		VCR accumulation	=	276.0	n.a.	PMID[492927]
NPT2	Others	Unspecified		VCR accumulation	=	692.0	n.a.	PMID[492927]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[492927]
NPT32	Organism	Mus musculus	Mus musculus	Median T/C	=	15.8	day	PMID[492927]
NPT32	Organism	Mus musculus	Mus musculus	Range	=	12.0	day	PMID[492927]
NPT32	Organism	Mus musculus	Mus musculus	T/C	=	138.0	%	PMID[492927]
NPT32	Organism	Mus musculus	Mus musculus	Median T/C	=	12.0	day	PMID[492927]
NPT32	Organism	Mus musculus	Mus musculus	Range	=	10.0	day	PMID[492927]
NPT32	Organism	Mus musculus	Mus musculus	T/C	=	105.0	%	PMID[492927]

☑ 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 NPC473423 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	313
0.1-0.2	1151
0.2-0.3	2155
0.3-0.4	5129
0.4-0.5	9402
0.5-0.6	17059
0.6-0.7	6566
0.7-0.8	813
0.8-0.85	83
0.85-0.9	20
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC469742
0.9431	High Similarity	NPC195224
0.936	High Similarity	NPC472361
0.9355	High Similarity	NPC225103
0.928	High Similarity	NPC472388
0.928	High Similarity	NPC473443
0.9225	High Similarity	NPC184109
0.9213	High Similarity	NPC472437
0.9206	High Similarity	NPC472418
0.9141	High Similarity	NPC4242
0.9141	High Similarity	NPC471911
0.9134	High Similarity	NPC475493
0.9134	High Similarity	NPC209851
0.9134	High Similarity	NPC472394
0.8984	High Similarity	NPC471880
0.8984	High Similarity	NPC80599
0.8943	High Similarity	NPC473749
0.8926	High Similarity	NPC89324
0.8864	High Similarity	NPC472371
0.8864	High Similarity	NPC472395
0.8862	High Similarity	NPC473439
0.8862	High Similarity	NPC300827
0.8815	High Similarity	NPC471912
0.8815	High Similarity	NPC80895
0.8797	High Similarity	NPC473440
0.875	High Similarity	NPC277053
0.875	High Similarity	NPC301946
0.872	High Similarity	NPC12016
0.8667	High Similarity	NPC475135
0.8661	High Similarity	NPC473082
0.8657	High Similarity	NPC475400
0.8651	High Similarity	NPC472373
0.8583	High Similarity	NPC471758
0.8583	High Similarity	NPC473083
0.8571	High Similarity	NPC472372
0.8571	High Similarity	NPC472374
0.8516	High Similarity	NPC470818
0.8516	High Similarity	NPC45821
0.8496	Intermediate Similarity	NPC477893
0.8394	Intermediate Similarity	NPC63737
0.8387	Intermediate Similarity	NPC152812
0.8358	Intermediate Similarity	NPC291638
0.8358	Intermediate Similarity	NPC17877
0.8358	Intermediate Similarity	NPC66761
0.8358	Intermediate Similarity	NPC195647
0.8358	Intermediate Similarity	NPC472577
0.8358	Intermediate Similarity	NPC477896
0.8346	Intermediate Similarity	NPC70973
0.8345	Intermediate Similarity	NPC127857
0.8345	Intermediate Similarity	NPC471107
0.8345	Intermediate Similarity	NPC471100
0.8333	Intermediate Similarity	NPC477894
0.8321	Intermediate Similarity	NPC93632
0.8284	Intermediate Similarity	NPC474608
0.8268	Intermediate Similarity	NPC311175
0.8268	Intermediate Similarity	NPC37641
0.8264	Intermediate Similarity	NPC21410
0.8264	Intermediate Similarity	NPC473670
0.8261	Intermediate Similarity	NPC34012
0.8261	Intermediate Similarity	NPC182869
0.8258	Intermediate Similarity	NPC147561
0.8248	Intermediate Similarity	NPC473109
0.8248	Intermediate Similarity	NPC43241
0.8248	Intermediate Similarity	NPC473758
0.8248	Intermediate Similarity	NPC476094
0.8248	Intermediate Similarity	NPC473613
0.8248	Intermediate Similarity	NPC211137
0.8248	Intermediate Similarity	NPC184747
0.8248	Intermediate Similarity	NPC473081
0.8248	Intermediate Similarity	NPC48017
0.8248	Intermediate Similarity	NPC473112
0.8248	Intermediate Similarity	NPC473060
0.8248	Intermediate Similarity	NPC473085
0.8248	Intermediate Similarity	NPC4341
0.8248	Intermediate Similarity	NPC200592
0.8248	Intermediate Similarity	NPC147880
0.824	Intermediate Similarity	NPC84129
0.8239	Intermediate Similarity	NPC7095
0.8239	Intermediate Similarity	NPC91730
0.8239	Intermediate Similarity	NPC112216
0.8239	Intermediate Similarity	NPC254558
0.8231	Intermediate Similarity	NPC473110
0.8231	Intermediate Similarity	NPC473111
0.8226	Intermediate Similarity	NPC476476
0.8217	Intermediate Similarity	NPC140118
0.8217	Intermediate Similarity	NPC12881
0.8214	Intermediate Similarity	NPC473541
0.8209	Intermediate Similarity	NPC15850
0.8207	Intermediate Similarity	NPC217091
0.8188	Intermediate Similarity	NPC16912
0.8182	Intermediate Similarity	NPC197037
0.8182	Intermediate Similarity	NPC51602
0.8175	Intermediate Similarity	NPC214550
0.8175	Intermediate Similarity	NPC475652
0.8175	Intermediate Similarity	NPC210591
0.8169	Intermediate Similarity	NPC60509
0.8169	Intermediate Similarity	NPC81698
0.8169	Intermediate Similarity	NPC250046
0.8168	Intermediate Similarity	NPC171007
0.8168	Intermediate Similarity	NPC190849
0.8156	Intermediate Similarity	NPC474935
0.8154	Intermediate Similarity	NPC114927
0.8151	Intermediate Similarity	NPC472393
0.8148	Intermediate Similarity	NPC329913
0.8143	Intermediate Similarity	NPC470231
0.8129	Intermediate Similarity	NPC140021
0.8116	Intermediate Similarity	NPC90614
0.8116	Intermediate Similarity	NPC97667
0.8116	Intermediate Similarity	NPC477904
0.8116	Intermediate Similarity	NPC183270
0.8116	Intermediate Similarity	NPC171207
0.8112	Intermediate Similarity	NPC165260
0.8112	Intermediate Similarity	NPC161239
0.8112	Intermediate Similarity	NPC198455
0.8102	Intermediate Similarity	NPC183122
0.8102	Intermediate Similarity	NPC283375
0.8102	Intermediate Similarity	NPC475373
0.8099	Intermediate Similarity	NPC217918
0.8092	Intermediate Similarity	NPC476970
0.8088	Intermediate Similarity	NPC473216
0.8088	Intermediate Similarity	NPC473399
0.8074	Intermediate Similarity	NPC472656
0.8071	Intermediate Similarity	NPC95449
0.8071	Intermediate Similarity	NPC475429
0.8071	Intermediate Similarity	NPC147217
0.8071	Intermediate Similarity	NPC191082
0.8071	Intermediate Similarity	NPC139067
0.8071	Intermediate Similarity	NPC473673
0.8071	Intermediate Similarity	NPC270498
0.8071	Intermediate Similarity	NPC246480
0.8071	Intermediate Similarity	NPC177340
0.8069	Intermediate Similarity	NPC1173
0.8069	Intermediate Similarity	NPC242262
0.8069	Intermediate Similarity	NPC158333
0.8069	Intermediate Similarity	NPC237549
0.8069	Intermediate Similarity	NPC219419
0.8069	Intermediate Similarity	NPC472005
0.8069	Intermediate Similarity	NPC11588
0.8069	Intermediate Similarity	NPC473414
0.8069	Intermediate Similarity	NPC229545
0.8069	Intermediate Similarity	NPC472030
0.8069	Intermediate Similarity	NPC472022
0.8069	Intermediate Similarity	NPC77719
0.8069	Intermediate Similarity	NPC256142
0.8069	Intermediate Similarity	NPC257213
0.8069	Intermediate Similarity	NPC248265
0.8069	Intermediate Similarity	NPC304876
0.8069	Intermediate Similarity	NPC249471
0.8069	Intermediate Similarity	NPC265395
0.8069	Intermediate Similarity	NPC134685
0.806	Intermediate Similarity	NPC476977
0.8058	Intermediate Similarity	NPC472576
0.8058	Intermediate Similarity	NPC87448
0.8058	Intermediate Similarity	NPC118080
0.8058	Intermediate Similarity	NPC291599
0.8058	Intermediate Similarity	NPC27377
0.8058	Intermediate Similarity	NPC41481
0.8058	Intermediate Similarity	NPC97947
0.8056	Intermediate Similarity	NPC306799
0.8056	Intermediate Similarity	NPC471103
0.8056	Intermediate Similarity	NPC101043
0.8031	Intermediate Similarity	NPC473860
0.803	Intermediate Similarity	NPC476972
0.803	Intermediate Similarity	NPC476971
0.803	Intermediate Similarity	NPC169913
0.8016	Intermediate Similarity	NPC470820
0.8015	Intermediate Similarity	NPC126516
0.8015	Intermediate Similarity	NPC48929
0.8014	Intermediate Similarity	NPC25768
0.8014	Intermediate Similarity	NPC114410
0.8014	Intermediate Similarity	NPC70716
0.8014	Intermediate Similarity	NPC95810
0.8014	Intermediate Similarity	NPC125106
0.8014	Intermediate Similarity	NPC472569
0.8014	Intermediate Similarity	NPC472570
0.8014	Intermediate Similarity	NPC476974
0.8014	Intermediate Similarity	NPC228204
0.8014	Intermediate Similarity	NPC51314
0.8014	Intermediate Similarity	NPC95265
0.8014	Intermediate Similarity	NPC155329
0.8014	Intermediate Similarity	NPC38696
0.8014	Intermediate Similarity	NPC26033
0.8014	Intermediate Similarity	NPC57628
0.8014	Intermediate Similarity	NPC114357
0.8014	Intermediate Similarity	NPC472573
0.8014	Intermediate Similarity	NPC67777
0.8014	Intermediate Similarity	NPC11685
0.8014	Intermediate Similarity	NPC111466
0.8014	Intermediate Similarity	NPC188865
0.8014	Intermediate Similarity	NPC259144
0.8014	Intermediate Similarity	NPC112523
0.8014	Intermediate Similarity	NPC163719
0.8014	Intermediate Similarity	NPC282239
0.8	Intermediate Similarity	NPC472548
0.8	Intermediate Similarity	NPC476976
0.8	Intermediate Similarity	NPC477905
0.8	Intermediate Similarity	NPC473869
0.7986	Intermediate Similarity	NPC100913
0.7986	Intermediate Similarity	NPC275592
0.7986	Intermediate Similarity	NPC472547

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 NPC473423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	776
0.2-0.3	1436
0.3-0.4	3076
0.4-0.5	2134
0.5-0.6	1243
0.6-0.7	202
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7698	Intermediate Similarity	NPD7094	Approved
0.7698	Intermediate Similarity	NPD6858	Approved
0.7554	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7236	Approved
0.7357	Intermediate Similarity	NPD7961	Discontinued
0.7338	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7239	Suspended
0.7329	Intermediate Similarity	NPD8166	Discontinued
0.7323	Intermediate Similarity	NPD2067	Discontinued
0.7295	Intermediate Similarity	NPD7798	Approved
0.7284	Intermediate Similarity	NPD8368	Discontinued
0.725	Intermediate Similarity	NPD7799	Discontinued
0.7239	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2629	Approved
0.7169	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8407	Phase 2
0.7132	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4198	Discontinued
0.7109	Intermediate Similarity	NPD2182	Approved
0.7103	Intermediate Similarity	NPD7305	Phase 1
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7083	Intermediate Similarity	NPD8435	Approved
0.7083	Intermediate Similarity	NPD8360	Approved
0.7083	Intermediate Similarity	NPD8361	Approved
0.708	Intermediate Similarity	NPD6637	Approved
0.7066	Intermediate Similarity	NPD8434	Phase 2
0.7063	Intermediate Similarity	NPD5909	Discontinued
0.7044	Intermediate Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD8032	Phase 2
0.6992	Remote Similarity	NPD3317	Approved
0.6984	Remote Similarity	NPD6647	Phase 2
0.6972	Remote Similarity	NPD7008	Discontinued
0.697	Remote Similarity	NPD6010	Discontinued
0.6933	Remote Similarity	NPD6190	Approved
0.6917	Remote Similarity	NPD5951	Approved
0.6899	Remote Similarity	NPD7058	Phase 2
0.6899	Remote Similarity	NPD7057	Phase 3
0.6884	Remote Similarity	NPD6287	Discontinued
0.688	Remote Similarity	NPD2066	Phase 3
0.6875	Remote Similarity	NPD6663	Approved
0.6875	Remote Similarity	NPD5048	Discontinued
0.6839	Remote Similarity	NPD8485	Approved
0.6839	Remote Similarity	NPD7458	Discontinued
0.6838	Remote Similarity	NPD7741	Discontinued
0.6831	Remote Similarity	NPD5736	Approved
0.6818	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD164	Approved
0.6779	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1989	Approved
0.6772	Remote Similarity	NPD7819	Suspended
0.6765	Remote Similarity	NPD7610	Discontinued
0.6761	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1929	Approved
0.6719	Remote Similarity	NPD1930	Approved
0.6718	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2438	Suspended
0.6711	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6685	Approved
0.669	Remote Similarity	NPD3764	Approved
0.6689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD3024	Approved
0.6645	Remote Similarity	NPD6273	Approved
0.6644	Remote Similarity	NPD7713	Phase 3
0.6642	Remote Similarity	NPD6065	Approved
0.6639	Remote Similarity	NPD3672	Approved
0.6639	Remote Similarity	NPD3673	Approved
0.6624	Remote Similarity	NPD3226	Approved
0.6619	Remote Similarity	NPD17	Approved
0.6619	Remote Similarity	NPD5125	Phase 3
0.6619	Remote Similarity	NPD5126	Approved
0.6619	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1238	Approved
0.6605	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD37	Approved
0.6603	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2979	Phase 3
0.6596	Remote Similarity	NPD3972	Approved
0.6587	Remote Similarity	NPD3495	Discontinued
0.6584	Remote Similarity	NPD4967	Phase 2
0.6584	Remote Similarity	NPD4966	Approved
0.6584	Remote Similarity	NPD4965	Approved
0.6582	Remote Similarity	NPD6599	Discontinued
0.6581	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3023	Approved
0.6571	Remote Similarity	NPD3026	Approved
0.6562	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7075	Discontinued
0.6536	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5926	Approved
0.6516	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1932	Approved
0.6503	Remote Similarity	NPD6234	Discontinued
0.65	Remote Similarity	NPD3019	Approved
0.6494	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8312	Approved
0.6491	Remote Similarity	NPD8313	Approved
0.6488	Remote Similarity	NPD5844	Phase 1
0.6485	Remote Similarity	NPD6232	Discontinued
0.6483	Remote Similarity	NPD7084	Phase 3
0.6481	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7900	Approved
0.6479	Remote Similarity	NPD1608	Approved
0.6475	Remote Similarity	NPD9545	Approved
0.6467	Remote Similarity	NPD7097	Phase 1
0.6466	Remote Similarity	NPD2329	Discontinued
0.6463	Remote Similarity	NPD5494	Approved
0.6462	Remote Similarity	NPD5765	Approved
0.6447	Remote Similarity	NPD2346	Discontinued
0.6447	Remote Similarity	NPD7266	Discontinued
0.6444	Remote Similarity	NPD6912	Phase 3
0.6443	Remote Similarity	NPD6355	Discontinued
0.6438	Remote Similarity	NPD6386	Approved
0.6438	Remote Similarity	NPD6385	Approved
0.6429	Remote Similarity	NPD5585	Approved
0.6429	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4110	Phase 3
0.6429	Remote Similarity	NPD7003	Approved
0.642	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7715	Approved
0.6419	Remote Similarity	NPD7714	Approved
0.6415	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6085	Phase 2
0.6414	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1281	Approved
0.6406	Remote Similarity	NPD7638	Approved
0.64	Remote Similarity	NPD7631	Approved
0.64	Remote Similarity	NPD1088	Approved
0.6398	Remote Similarity	NPD6801	Discontinued
0.6395	Remote Similarity	NPD7095	Approved
0.6393	Remote Similarity	NPD1087	Approved
0.6391	Remote Similarity	NPD6686	Approved
0.6389	Remote Similarity	NPD5667	Approved
0.6383	Remote Similarity	NPD2932	Approved
0.6382	Remote Similarity	NPD6099	Approved
0.6382	Remote Similarity	NPD6100	Approved
0.6382	Remote Similarity	NPD2796	Approved
0.6376	Remote Similarity	NPD4140	Approved
0.6375	Remote Similarity	NPD4380	Phase 2
0.6374	Remote Similarity	NPD6765	Approved
0.6374	Remote Similarity	NPD6764	Approved
0.6364	Remote Similarity	NPD6008	Approved
0.6358	Remote Similarity	NPD8455	Phase 2
0.6358	Remote Similarity	NPD5761	Phase 2
0.6358	Remote Similarity	NPD5760	Phase 2
0.6357	Remote Similarity	NPD7640	Approved
0.6357	Remote Similarity	NPD7639	Approved
0.6351	Remote Similarity	NPD6798	Discontinued
0.6351	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3267	Approved
0.6345	Remote Similarity	NPD3266	Approved
0.6336	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7411	Suspended
0.6333	Remote Similarity	NPD230	Phase 1
0.6331	Remote Similarity	NPD7228	Approved
0.6329	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7902	Approved
0.6324	Remote Similarity	NPD8297	Approved
0.632	Remote Similarity	NPD7609	Phase 3
0.6319	Remote Similarity	NPD3817	Phase 2
0.6319	Remote Similarity	NPD5327	Phase 3
0.6316	Remote Similarity	NPD2799	Discontinued
0.6316	Remote Similarity	NPD3748	Approved
0.6316	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5691	Approved
0.6312	Remote Similarity	NPD1651	Approved
0.6309	Remote Similarity	NPD6233	Phase 2
0.6306	Remote Similarity	NPD6799	Approved
0.6304	Remote Similarity	NPD4766	Approved
0.6299	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1693	Approved
0.6299	Remote Similarity	NPD6049	Phase 2
0.6296	Remote Similarity	NPD4233	Approved
0.6296	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4234	Approved
0.6294	Remote Similarity	NPD4807	Approved
0.6294	Remote Similarity	NPD4806	Approved
0.6287	Remote Similarity	NPD7229	Phase 3
0.6282	Remote Similarity	NPD3887	Approved
0.6279	Remote Similarity	NPD7685	Pre-registration
0.6276	Remote Similarity	NPD1283	Approved
0.6275	Remote Similarity	NPD2531	Phase 2
0.6268	Remote Similarity	NPD5305	Approved
0.6268	Remote Similarity	NPD5306	Approved
0.6266	Remote Similarity	NPD2533	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data