NPASS Compound

Structure

CID273433 OpenBabel06191716082D 36 38 0 0 1 0 0 0 0 0999 V2000 0.8227 -2.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6790 0.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5065 2.7507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1355 -2.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9806 1.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 -0.2035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7870 -0.3174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -0.7849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3556 -1.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -0.6025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9142 2.0080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2277 -3.1147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2842 2.0785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -0.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1921 -1.5373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 0.4750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0811 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6689 0.3809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7427 -1.5423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7427 0.5923 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7212 -1.2651 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 -1.6689 -1.3309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9748 2.1496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0163 -4.0408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4956 3.0047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 -1.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0481 -1.9494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 1.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1904 -2.0530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2612 1.1237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5313 -2.4685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5313 1.5185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 24 1 0 0 0 0 7 24 1 0 0 0 0 9 16 1 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 26 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 0 0 0 0 13 27 2 0 0 0 0 13 34 1 0 0 0 0 14 28 2 0 0 0 0 14 35 1 0 0 0 0 15 29 2 0 0 0 0 15 36 1 0 0 0 0 16 30 1 6 0 0 0 17 31 2 0 0 0 0 18 25 1 1 0 0 0 18 32 1 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 25 1 1 0 0 0 21 23 1 0 0 0 0 21 34 1 1 0 0 0 22 26 1 6 0 0 0 22 35 1 0 0 0 0 23 25 1 6 0 0 0 23 36 1 0 0 0 0 24 33 1 0 0 0 0 25 8 1 1 0 0 0 26 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.23
Volume:	504.666
LogP:	1.078
LogD:	0.759
LogS:	-3.425
# Rotatable Bonds:	7
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.288
Synthetic Accessibility Score:	5.337
Fsp3:	0.692
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:	-5.387
MDCK Permeability:	0.00010954161552945152
Pgp-inhibitor:	0.963
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.397
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.226

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	51.57331848144531%
Volume Distribution (VD):	0.782
Pgp-substrate:	41.82081985473633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	2.589
Half-life (T1/2):	0.742

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.662
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.205
Carcinogencity:	0.221
Eye Corrosion:	0.017
Eye Irritation:	0.033
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC273433

Natural Product ID:	NPC273433
*Common Name:**	[(4R,5R,5As,6S,8S,9Ar,10S,10As)-5,10-Diacetyloxy-6,8-Dihydroxy-10A-(2-Hydroxypropan-2-Yl)-3,5A-Dimethyl-9-Methylidene-2-Oxo-1,4,5,6,7,8,9A,10-Octahydrobenzo[G]Azulen-4-Yl] Acetate
IUPAC Name:	[(4R,5R,5aS,6S,8S,9aR,10S,10aS)-5,10-diacetyloxy-6,8-dihydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2-oxo-1,4,5,6,7,8,9a,10-octahydrobenzo[g]azulen-4-yl] acetate
Synonyms:
Standard InCHIKey:	YBKLIOKMYMZPJB-MDWMNUHPSA-N
Standard InCHI:	InChI=1S/C26H36O10/c1-11-16(30)9-18(32)25(8)20(11)22(35-14(4)28)26(24(6,7)33)10-17(31)12(2)19(26)21(34-13(3)27)23(25)36-15(5)29/h16,18,20-23,30,32-33H,1,9-10H2,2-8H3/t16-,18-,20-,21+,22-,23-,25+,26-/m0/s1
SMILES:	C=C1[C@H](C[C@@H]([C@]2(C)[C@@H]1[C@@H]([C@@]1(CC(=O)C(=C1[C@H]([C@@H]2OC(=O)C)OC(=O)C)C)C(C)(C)O)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL367055
PubChem CID:	5321756
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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[454377]
NPT2	Others	Unspecified		Control	=	151.0	%	PMID[454377]
NPT2	Others	Unspecified		Control	=	191.0	%	PMID[454377]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[454377]

☑ 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 NPC273433 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	230
0.1-0.2	1421
0.2-0.3	4177
0.3-0.4	6772
0.4-0.5	13727
0.5-0.6	8350
0.6-0.7	6265
0.7-0.8	1627
0.8-0.85	117
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8727	High Similarity	NPC234858
0.8727	High Similarity	NPC471127
0.8727	High Similarity	NPC154363
0.8679	High Similarity	NPC143609
0.8649	High Similarity	NPC10721
0.8585	High Similarity	NPC111952
0.8584	High Similarity	NPC471128
0.8584	High Similarity	NPC157252
0.8584	High Similarity	NPC145182
0.8584	High Similarity	NPC471126
0.8545	High Similarity	NPC472757
0.8522	High Similarity	NPC472399
0.8509	High Similarity	NPC52839
0.8505	High Similarity	NPC187435
0.8505	High Similarity	NPC67321
0.8496	Intermediate Similarity	NPC156745
0.8496	Intermediate Similarity	NPC236918
0.8468	Intermediate Similarity	NPC472400
0.8447	Intermediate Similarity	NPC254121
0.8421	Intermediate Similarity	NPC475885
0.8421	Intermediate Similarity	NPC472759
0.8421	Intermediate Similarity	NPC329080
0.8407	Intermediate Similarity	NPC124676
0.8407	Intermediate Similarity	NPC472758
0.8407	Intermediate Similarity	NPC146280
0.8407	Intermediate Similarity	NPC471125
0.8407	Intermediate Similarity	NPC472397
0.8407	Intermediate Similarity	NPC171905
0.84	Intermediate Similarity	NPC209816
0.8396	Intermediate Similarity	NPC8196
0.8378	Intermediate Similarity	NPC471204
0.835	Intermediate Similarity	NPC475304
0.8348	Intermediate Similarity	NPC472401
0.8333	Intermediate Similarity	NPC5991
0.8333	Intermediate Similarity	NPC472667
0.8333	Intermediate Similarity	NPC469380
0.8333	Intermediate Similarity	NPC5989
0.8333	Intermediate Similarity	NPC22628
0.8333	Intermediate Similarity	NPC471108
0.8333	Intermediate Similarity	NPC255081
0.8333	Intermediate Similarity	NPC275696
0.8317	Intermediate Similarity	NPC249034
0.8304	Intermediate Similarity	NPC474872
0.8302	Intermediate Similarity	NPC476081
0.8302	Intermediate Similarity	NPC137430
0.8302	Intermediate Similarity	NPC474709
0.8302	Intermediate Similarity	NPC295791
0.8291	Intermediate Similarity	NPC473919
0.8291	Intermediate Similarity	NPC145238
0.8291	Intermediate Similarity	NPC473709
0.8286	Intermediate Similarity	NPC474718
0.8276	Intermediate Similarity	NPC162009
0.8276	Intermediate Similarity	NPC257017
0.8276	Intermediate Similarity	NPC19464
0.8257	Intermediate Similarity	NPC476479
0.8257	Intermediate Similarity	NPC306265
0.8257	Intermediate Similarity	NPC151393
0.8252	Intermediate Similarity	NPC292178
0.8252	Intermediate Similarity	NPC86893
0.8224	Intermediate Similarity	NPC99266
0.8214	Intermediate Similarity	NPC71889
0.8214	Intermediate Similarity	NPC25909
0.8205	Intermediate Similarity	NPC473802
0.8198	Intermediate Similarity	NPC469655
0.8198	Intermediate Similarity	NPC469656
0.8198	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC159456
0.819	Intermediate Similarity	NPC4021
0.8182	Intermediate Similarity	NPC42662
0.8174	Intermediate Similarity	NPC475041
0.8173	Intermediate Similarity	NPC202833
0.8165	Intermediate Similarity	NPC112780
0.8158	Intermediate Similarity	NPC55296
0.8158	Intermediate Similarity	NPC469684
0.8158	Intermediate Similarity	NPC156252
0.8158	Intermediate Similarity	NPC475323
0.8158	Intermediate Similarity	NPC473656
0.8151	Intermediate Similarity	NPC471940
0.8148	Intermediate Similarity	NPC118911
0.8148	Intermediate Similarity	NPC203659
0.8131	Intermediate Similarity	NPC165578
0.8125	Intermediate Similarity	NPC269530
0.8125	Intermediate Similarity	NPC317687
0.8125	Intermediate Similarity	NPC475391
0.8125	Intermediate Similarity	NPC472002
0.812	Intermediate Similarity	NPC269642
0.8108	Intermediate Similarity	NPC5103
0.8103	Intermediate Similarity	NPC154491
0.8103	Intermediate Similarity	NPC251226
0.8103	Intermediate Similarity	NPC19336
0.8103	Intermediate Similarity	NPC143755
0.8103	Intermediate Similarity	NPC268530
0.8103	Intermediate Similarity	NPC185876
0.8103	Intermediate Similarity	NPC48692
0.8091	Intermediate Similarity	NPC472439
0.8091	Intermediate Similarity	NPC469916
0.8083	Intermediate Similarity	NPC236999
0.8077	Intermediate Similarity	NPC36954
0.8073	Intermediate Similarity	NPC470975
0.8073	Intermediate Similarity	NPC243998
0.8073	Intermediate Similarity	NPC470979
0.8073	Intermediate Similarity	NPC103088
0.8073	Intermediate Similarity	NPC223450
0.807	Intermediate Similarity	NPC176840
0.807	Intermediate Similarity	NPC476710
0.807	Intermediate Similarity	NPC476711
0.8067	Intermediate Similarity	NPC293112
0.8067	Intermediate Similarity	NPC471939
0.8058	Intermediate Similarity	NPC135776
0.8056	Intermediate Similarity	NPC110989
0.8056	Intermediate Similarity	NPC159533
0.8056	Intermediate Similarity	NPC120321
0.8053	Intermediate Similarity	NPC469496
0.8053	Intermediate Similarity	NPC469454
0.8053	Intermediate Similarity	NPC474937
0.8053	Intermediate Similarity	NPC469463
0.8053	Intermediate Similarity	NPC962
0.8053	Intermediate Similarity	NPC250109
0.8051	Intermediate Similarity	NPC469382
0.8051	Intermediate Similarity	NPC67251
0.8051	Intermediate Similarity	NPC469789
0.8037	Intermediate Similarity	NPC471412
0.8037	Intermediate Similarity	NPC97435
0.8036	Intermediate Similarity	NPC475480
0.8036	Intermediate Similarity	NPC96739
0.8036	Intermediate Similarity	NPC158523
0.8036	Intermediate Similarity	NPC475668
0.8036	Intermediate Similarity	NPC174471
0.8036	Intermediate Similarity	NPC473921
0.8036	Intermediate Similarity	NPC317107
0.8036	Intermediate Similarity	NPC474871
0.8036	Intermediate Similarity	NPC475937
0.8036	Intermediate Similarity	NPC287311
0.8036	Intermediate Similarity	NPC260786
0.8034	Intermediate Similarity	NPC310511
0.8018	Intermediate Similarity	NPC474243
0.8017	Intermediate Similarity	NPC180640
0.8017	Intermediate Similarity	NPC312536
0.8017	Intermediate Similarity	NPC230513
0.8	Intermediate Similarity	NPC476712
0.8	Intermediate Similarity	NPC473173
0.8	Intermediate Similarity	NPC469318
0.8	Intermediate Similarity	NPC476713
0.8	Intermediate Similarity	NPC476315
0.8	Intermediate Similarity	NPC473590
0.8	Intermediate Similarity	NPC473968
0.7983	Intermediate Similarity	NPC81736
0.7983	Intermediate Similarity	NPC86346
0.7983	Intermediate Similarity	NPC469379
0.7983	Intermediate Similarity	NPC172154
0.7983	Intermediate Similarity	NPC476729
0.7983	Intermediate Similarity	NPC75856
0.7982	Intermediate Similarity	NPC90472
0.7982	Intermediate Similarity	NPC65523
0.7982	Intermediate Similarity	NPC473798
0.7982	Intermediate Similarity	NPC258532
0.7982	Intermediate Similarity	NPC181145
0.7982	Intermediate Similarity	NPC100487
0.7966	Intermediate Similarity	NPC222688
0.7966	Intermediate Similarity	NPC470265
0.7966	Intermediate Similarity	NPC23786
0.7965	Intermediate Similarity	NPC89227
0.7965	Intermediate Similarity	NPC265499
0.7965	Intermediate Similarity	NPC470063
0.7965	Intermediate Similarity	NPC473877
0.7965	Intermediate Similarity	NPC101825
0.7965	Intermediate Similarity	NPC474516
0.7965	Intermediate Similarity	NPC151216
0.7965	Intermediate Similarity	NPC221511
0.7965	Intermediate Similarity	NPC234042
0.7965	Intermediate Similarity	NPC215643
0.7965	Intermediate Similarity	NPC17138
0.7965	Intermediate Similarity	NPC152117
0.7965	Intermediate Similarity	NPC170212
0.7963	Intermediate Similarity	NPC472552
0.7963	Intermediate Similarity	NPC162973
0.7963	Intermediate Similarity	NPC478156
0.7963	Intermediate Similarity	NPC86077
0.7963	Intermediate Similarity	NPC225353
0.7949	Intermediate Similarity	NPC475003
0.7946	Intermediate Similarity	NPC472214
0.7946	Intermediate Similarity	NPC257240
0.7946	Intermediate Similarity	NPC253906
0.7946	Intermediate Similarity	NPC477103
0.7946	Intermediate Similarity	NPC478211
0.7946	Intermediate Similarity	NPC475134
0.7946	Intermediate Similarity	NPC475563
0.7946	Intermediate Similarity	NPC153036
0.7946	Intermediate Similarity	NPC472215
0.7944	Intermediate Similarity	NPC471413
0.7944	Intermediate Similarity	NPC274643
0.7944	Intermediate Similarity	NPC306856
0.7944	Intermediate Similarity	NPC475877
0.7944	Intermediate Similarity	NPC38855
0.7944	Intermediate Similarity	NPC47024
0.7941	Intermediate Similarity	NPC32922
0.7934	Intermediate Similarity	NPC270109
0.7931	Intermediate Similarity	NPC472760
0.7931	Intermediate Similarity	NPC251310
0.7931	Intermediate Similarity	NPC475372

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 NPC273433 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1876
0.2-0.3	3590
0.3-0.4	2213
0.4-0.5	822
0.5-0.6	283
0.6-0.7	157
0.7-0.8	9
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
0.7946	Intermediate Similarity	NPD6371	Approved
0.7679	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7640	Approved
0.7615	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5344	Discontinued
0.7544	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7115	Discovery
0.7524	Intermediate Similarity	NPD6698	Approved
0.7524	Intermediate Similarity	NPD46	Approved
0.7523	Intermediate Similarity	NPD7638	Approved
0.7523	Intermediate Similarity	NPD4225	Approved
0.748	Intermediate Similarity	NPD7507	Approved
0.7456	Intermediate Similarity	NPD6686	Approved
0.744	Intermediate Similarity	NPD7319	Approved
0.7391	Intermediate Similarity	NPD6372	Approved
0.7391	Intermediate Similarity	NPD6373	Approved
0.7368	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD8297	Approved
0.7304	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6648	Approved
0.7281	Intermediate Similarity	NPD5739	Approved
0.7281	Intermediate Similarity	NPD6675	Approved
0.7281	Intermediate Similarity	NPD6402	Approved
0.7281	Intermediate Similarity	NPD7128	Approved
0.7265	Intermediate Similarity	NPD6649	Approved
0.7265	Intermediate Similarity	NPD6650	Approved
0.7213	Intermediate Similarity	NPD6319	Approved
0.7203	Intermediate Similarity	NPD6053	Discontinued
0.7168	Intermediate Similarity	NPD7632	Discontinued
0.7155	Intermediate Similarity	NPD6881	Approved
0.7155	Intermediate Similarity	NPD6899	Approved
0.7155	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.713	Intermediate Similarity	NPD7983	Approved
0.713	Intermediate Similarity	NPD6008	Approved
0.7069	Intermediate Similarity	NPD5701	Approved
0.7069	Intermediate Similarity	NPD5697	Approved
0.7064	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD5778	Approved
0.7059	Intermediate Similarity	NPD6882	Approved
0.7049	Intermediate Similarity	NPD7327	Approved
0.7049	Intermediate Similarity	NPD7328	Approved
0.7037	Intermediate Similarity	NPD5785	Approved
0.7034	Intermediate Similarity	NPD6883	Approved
0.7034	Intermediate Similarity	NPD7290	Approved
0.7034	Intermediate Similarity	NPD7102	Approved
0.7016	Intermediate Similarity	NPD8515	Approved
0.7016	Intermediate Similarity	NPD8517	Approved
0.7016	Intermediate Similarity	NPD8513	Phase 3
0.7016	Intermediate Similarity	NPD8516	Approved
0.6992	Remote Similarity	NPD7516	Approved
0.6984	Remote Similarity	NPD7492	Approved
0.6975	Remote Similarity	NPD8130	Phase 1
0.6975	Remote Similarity	NPD6617	Approved
0.6975	Remote Similarity	NPD6869	Approved
0.6975	Remote Similarity	NPD6847	Approved
0.6967	Remote Similarity	NPD6009	Approved
0.6949	Remote Similarity	NPD6012	Approved
0.6949	Remote Similarity	NPD6013	Approved
0.6949	Remote Similarity	NPD6014	Approved
0.6944	Remote Similarity	NPD1695	Approved
0.6935	Remote Similarity	NPD6059	Approved
0.6935	Remote Similarity	NPD6054	Approved
0.6929	Remote Similarity	NPD6616	Approved
0.6909	Remote Similarity	NPD6399	Phase 3
0.6905	Remote Similarity	NPD8328	Phase 3
0.6905	Remote Similarity	NPD7604	Phase 2
0.6903	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7838	Discovery
0.688	Remote Similarity	NPD8379	Approved
0.688	Remote Similarity	NPD8296	Approved
0.688	Remote Similarity	NPD5983	Phase 2
0.688	Remote Similarity	NPD8033	Approved
0.688	Remote Similarity	NPD8378	Approved
0.688	Remote Similarity	NPD8380	Approved
0.688	Remote Similarity	NPD8335	Approved
0.6875	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD8293	Discontinued
0.687	Remote Similarity	NPD5211	Phase 2
0.6864	Remote Similarity	NPD6011	Approved
0.6847	Remote Similarity	NPD5282	Discontinued
0.6833	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6370	Approved
0.6822	Remote Similarity	NPD7736	Approved
0.6818	Remote Similarity	NPD7637	Suspended
0.6814	Remote Similarity	NPD4755	Approved
0.6814	Remote Similarity	NPD7902	Approved
0.6807	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8294	Approved
0.68	Remote Similarity	NPD8377	Approved
0.6797	Remote Similarity	NPD6336	Discontinued
0.6794	Remote Similarity	NPD7260	Phase 2
0.6789	Remote Similarity	NPD5328	Approved
0.678	Remote Similarity	NPD6412	Phase 2
0.6752	Remote Similarity	NPD5141	Approved
0.6746	Remote Similarity	NPD6016	Approved
0.6746	Remote Similarity	NPD6015	Approved
0.6746	Remote Similarity	NPD6921	Approved
0.6744	Remote Similarity	NPD8074	Phase 3
0.6729	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1694	Approved
0.6721	Remote Similarity	NPD8133	Approved
0.6698	Remote Similarity	NPD7154	Phase 3
0.6696	Remote Similarity	NPD5286	Approved
0.6696	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD5285	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD4696	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6845	Suspended
0.6614	Remote Similarity	NPD7503	Approved
0.6613	Remote Similarity	NPD6274	Approved
0.6612	Remote Similarity	NPD4634	Approved
0.6606	Remote Similarity	NPD7524	Approved
0.6604	Remote Similarity	NPD6435	Approved
0.6604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7100	Approved
0.6587	Remote Similarity	NPD7101	Approved
0.6581	Remote Similarity	NPD5224	Approved
0.6581	Remote Similarity	NPD5226	Approved
0.6581	Remote Similarity	NPD4633	Approved
0.6581	Remote Similarity	NPD5225	Approved
0.6579	Remote Similarity	NPD4697	Phase 3
0.6574	Remote Similarity	NPD5363	Approved
0.6555	Remote Similarity	NPD4767	Approved
0.6555	Remote Similarity	NPD4768	Approved
0.6549	Remote Similarity	NPD7900	Approved
0.6549	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6695	Phase 3
0.6542	Remote Similarity	NPD5362	Discontinued
0.6538	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5174	Approved
0.6525	Remote Similarity	NPD5175	Approved
0.6518	Remote Similarity	NPD8035	Phase 2
0.6518	Remote Similarity	NPD8034	Phase 2
0.6508	Remote Similarity	NPD6335	Approved
0.6496	Remote Similarity	NPD5223	Approved
0.6491	Remote Similarity	NPD5695	Phase 3
0.6486	Remote Similarity	NPD6101	Approved
0.6486	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6909	Approved
0.6484	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD5696	Approved
0.646	Remote Similarity	NPD4202	Approved
0.6455	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD4250	Approved
0.6449	Remote Similarity	NPD4269	Approved
0.6449	Remote Similarity	NPD4270	Approved
0.6446	Remote Similarity	NPD4729	Approved
0.6446	Remote Similarity	NPD4730	Approved
0.6439	Remote Similarity	NPD6033	Approved
0.6435	Remote Similarity	NPD5222	Approved
0.6435	Remote Similarity	NPD7839	Suspended
0.6435	Remote Similarity	NPD5221	Approved
0.6435	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6317	Approved
0.6415	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4821	Approved
0.6415	Remote Similarity	NPD4819	Approved
0.6415	Remote Similarity	NPD5368	Approved
0.6415	Remote Similarity	NPD4822	Approved
0.6415	Remote Similarity	NPD4820	Approved
0.6387	Remote Similarity	NPD4754	Approved
0.6379	Remote Similarity	NPD5173	Approved
0.6378	Remote Similarity	NPD6313	Approved
0.6378	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6357	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5369	Approved
0.6349	Remote Similarity	NPD6868	Approved
0.6348	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5249	Phase 3
0.6341	Remote Similarity	NPD5250	Approved
0.6341	Remote Similarity	NPD5251	Approved
0.6341	Remote Similarity	NPD5248	Approved
0.6341	Remote Similarity	NPD5247	Approved
0.633	Remote Similarity	NPD4786	Approved
0.633	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5128	Approved
0.6306	Remote Similarity	NPD7750	Discontinued
0.6306	Remote Similarity	NPD3573	Approved
0.6296	Remote Similarity	NPD3667	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