NPASS Compound

Structure

CID284365 OpenBabel06191716092D 35 37 0 0 1 0 0 0 0 0999 V2000 2.2729 2.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5462 2.6247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5296 -1.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0141 -0.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7574 -0.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5151 -0.8751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4374 -0.7577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5155 -1.7499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0307 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7578 -1.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 -0.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2729 1.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7884 2.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8422 -1.4249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1996 -0.5455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 -1.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2729 -0.4377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.7499 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0307 0.8748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2729 -1.3127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7578 -0.4375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5152 0.8748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7574 1.3122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5151 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0307 2.6247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9666 -0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0692 -1.4107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 -2.6249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7574 2.1871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7577 1.3124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7884 1.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0302 -1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5155 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 8 16 2 0 0 0 0 8 20 1 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 26 1 0 0 0 0 12 19 1 0 0 0 0 12 22 2 0 0 0 0 13 27 2 0 0 0 0 13 33 1 0 0 0 0 14 28 2 0 0 0 0 14 34 1 0 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 18 1 0 0 0 0 17 9 1 1 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 30 1 1 0 0 0 19 33 1 1 0 0 0 20 34 1 1 0 0 0 21 26 1 6 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 6 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 26 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	495.876
LogP:	2.294
LogD:	2.272
LogS:	-4.287
# Rotatable Bonds:	6
TPSA:	133.27
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	6.47
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.106
MDCK Permeability:	0.0001019098999677226
Pgp-inhibitor:	0.999
Pgp-substrate:	0.294
Human Intestinal Absorption (HIA):	0.775
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	72.77342987060547%
Volume Distribution (VD):	0.541
Pgp-substrate:	24.112464904785156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.159
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.42
CYP3A4-substrate:	0.399

ADMET: Excretion

Clearance (CL):	2.996
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.877
Drug-inuced Liver Injury (DILI):	0.648
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.652
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.127
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC284365

Natural Product ID:	NPC284365
*Common Name:**	Taxuspine W
IUPAC Name:	n.a.
Synonyms:	taxuspine W
Standard InCHIKey:	ZUIZFJGNEDXNJD-MKSBNKCPSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-12-19(33-13(2)27)9-17-20(34-14(3)28)8-16-11-26(7,21(10-18(16)30)35-15(4)29)24(32)23(31)22(12)25(17,5)6/h8,17-21,23,30-31H,9-11H2,1-7H3/b16-8+/t17-,18-,19-,20-,21-,23+,26-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@H](OC(=O)C)/C=C/3C[C@@](C(=O)[C@@H](C(=C1C)C2(C)C)O)(C)[C@H](C[C@@H]3O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490154
PubChem CID:	5321766
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.08	ug.mL-1	PMID[548777]

☑ 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 NPC284365 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	211
0.1-0.2	1282
0.2-0.3	4345
0.3-0.4	7133
0.4-0.5	14305
0.5-0.6	8214
0.6-0.7	6157
0.7-0.8	1031
0.8-0.85	15
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC123726
0.9388	High Similarity	NPC476478
0.9216	High Similarity	NPC476479
0.8411	Intermediate Similarity	NPC42662
0.8318	Intermediate Similarity	NPC322903
0.8302	Intermediate Similarity	NPC111952
0.8235	Intermediate Similarity	NPC202833
0.8224	Intermediate Similarity	NPC112780
0.8224	Intermediate Similarity	NPC143609
0.8208	Intermediate Similarity	NPC258532
0.819	Intermediate Similarity	NPC476729
0.8182	Intermediate Similarity	NPC473877
0.8182	Intermediate Similarity	NPC90952
0.8182	Intermediate Similarity	NPC317687
0.8173	Intermediate Similarity	NPC306856
0.8173	Intermediate Similarity	NPC474718
0.8173	Intermediate Similarity	NPC174314
0.8165	Intermediate Similarity	NPC161816
0.8165	Intermediate Similarity	NPC115257
0.8155	Intermediate Similarity	NPC254496
0.8155	Intermediate Similarity	NPC285513
0.8142	Intermediate Similarity	NPC251310
0.8137	Intermediate Similarity	NPC471786
0.8137	Intermediate Similarity	NPC37603
0.8137	Intermediate Similarity	NPC266899
0.8131	Intermediate Similarity	NPC1679
0.8113	Intermediate Similarity	NPC69171
0.8113	Intermediate Similarity	NPC474165
0.8108	Intermediate Similarity	NPC472926
0.8108	Intermediate Similarity	NPC159333
0.8103	Intermediate Similarity	NPC105926
0.8103	Intermediate Similarity	NPC18945
0.8103	Intermediate Similarity	NPC67251
0.8103	Intermediate Similarity	NPC91693
0.8103	Intermediate Similarity	NPC265557
0.8095	Intermediate Similarity	NPC111292
0.8091	Intermediate Similarity	NPC317107
0.8073	Intermediate Similarity	NPC475922
0.8073	Intermediate Similarity	NPC474243
0.8053	Intermediate Similarity	NPC176513
0.8053	Intermediate Similarity	NPC470775
0.8053	Intermediate Similarity	NPC473590
0.8037	Intermediate Similarity	NPC220964
0.8037	Intermediate Similarity	NPC239162
0.8037	Intermediate Similarity	NPC475676
0.8034	Intermediate Similarity	NPC470922
0.8019	Intermediate Similarity	NPC474709
0.8019	Intermediate Similarity	NPC183571
0.8019	Intermediate Similarity	NPC478156
0.8018	Intermediate Similarity	NPC277769
0.8017	Intermediate Similarity	NPC312833
0.8	Intermediate Similarity	NPC476933
0.8	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC477521
0.7982	Intermediate Similarity	NPC89171
0.7982	Intermediate Similarity	NPC470776
0.7982	Intermediate Similarity	NPC476802
0.7982	Intermediate Similarity	NPC21326
0.7982	Intermediate Similarity	NPC151393
0.7981	Intermediate Similarity	NPC287668
0.7965	Intermediate Similarity	NPC476710
0.7965	Intermediate Similarity	NPC474333
0.7965	Intermediate Similarity	NPC476711
0.7965	Intermediate Similarity	NPC474734
0.7963	Intermediate Similarity	NPC28791
0.7963	Intermediate Similarity	NPC295366
0.7961	Intermediate Similarity	NPC134067
0.7949	Intermediate Similarity	NPC472399
0.7946	Intermediate Similarity	NPC469496
0.7946	Intermediate Similarity	NPC469463
0.7946	Intermediate Similarity	NPC208998
0.7946	Intermediate Similarity	NPC471204
0.7946	Intermediate Similarity	NPC25909
0.7946	Intermediate Similarity	NPC469454
0.7946	Intermediate Similarity	NPC7921
0.7944	Intermediate Similarity	NPC4620
0.7944	Intermediate Similarity	NPC95899
0.7944	Intermediate Similarity	NPC8196
0.7944	Intermediate Similarity	NPC90177
0.7941	Intermediate Similarity	NPC99653
0.7931	Intermediate Similarity	NPC470779
0.7928	Intermediate Similarity	NPC146945
0.7928	Intermediate Similarity	NPC171888
0.7925	Intermediate Similarity	NPC471412
0.7921	Intermediate Similarity	NPC232202
0.7913	Intermediate Similarity	NPC476529
0.7913	Intermediate Similarity	NPC472933
0.7913	Intermediate Similarity	NPC470186
0.7913	Intermediate Similarity	NPC475775
0.7909	Intermediate Similarity	NPC141350
0.7905	Intermediate Similarity	NPC216478
0.7895	Intermediate Similarity	NPC469684
0.7895	Intermediate Similarity	NPC296822
0.7895	Intermediate Similarity	NPC476712
0.7895	Intermediate Similarity	NPC476713
0.7895	Intermediate Similarity	NPC134430
0.7895	Intermediate Similarity	NPC472927
0.789	Intermediate Similarity	NPC475510
0.789	Intermediate Similarity	NPC251824
0.789	Intermediate Similarity	NPC475587
0.789	Intermediate Similarity	NPC472925
0.789	Intermediate Similarity	NPC86852
0.7885	Intermediate Similarity	NPC284194
0.7885	Intermediate Similarity	NPC211810
0.7885	Intermediate Similarity	NPC471765
0.7885	Intermediate Similarity	NPC221801
0.7885	Intermediate Similarity	NPC184065
0.7881	Intermediate Similarity	NPC24651
0.7876	Intermediate Similarity	NPC117712
0.7876	Intermediate Similarity	NPC469877
0.7876	Intermediate Similarity	NPC470919
0.7876	Intermediate Similarity	NPC181145
0.787	Intermediate Similarity	NPC470104
0.787	Intermediate Similarity	NPC475036
0.787	Intermediate Similarity	NPC47281
0.787	Intermediate Similarity	NPC118911
0.7864	Intermediate Similarity	NPC250075
0.7857	Intermediate Similarity	NPC302146
0.7857	Intermediate Similarity	NPC4573
0.7857	Intermediate Similarity	NPC269530
0.785	Intermediate Similarity	NPC476081
0.785	Intermediate Similarity	NPC162973
0.785	Intermediate Similarity	NPC137430
0.785	Intermediate Similarity	NPC295791
0.785	Intermediate Similarity	NPC164551
0.785	Intermediate Similarity	NPC475091
0.7845	Intermediate Similarity	NPC472004
0.7845	Intermediate Similarity	NPC112038
0.7845	Intermediate Similarity	NPC107338
0.7845	Intermediate Similarity	NPC109607
0.7843	Intermediate Similarity	NPC124374
0.7843	Intermediate Similarity	NPC473944
0.7838	Intermediate Similarity	NPC83005
0.783	Intermediate Similarity	NPC293890
0.783	Intermediate Similarity	NPC54705
0.783	Intermediate Similarity	NPC472972
0.783	Intermediate Similarity	NPC472644
0.783	Intermediate Similarity	NPC471413
0.783	Intermediate Similarity	NPC117685
0.7818	Intermediate Similarity	NPC233379
0.7818	Intermediate Similarity	NPC289702
0.7818	Intermediate Similarity	NPC14862
0.7818	Intermediate Similarity	NPC94377
0.7818	Intermediate Similarity	NPC208461
0.7818	Intermediate Similarity	NPC473939
0.7818	Intermediate Similarity	NPC189075
0.7818	Intermediate Similarity	NPC275539
0.7818	Intermediate Similarity	NPC474664
0.7818	Intermediate Similarity	NPC473595
0.7818	Intermediate Similarity	NPC293850
0.7815	Intermediate Similarity	NPC181999
0.781	Intermediate Similarity	NPC53844
0.781	Intermediate Similarity	NPC474395
0.781	Intermediate Similarity	NPC473244
0.7807	Intermediate Similarity	NPC270478
0.7807	Intermediate Similarity	NPC470628
0.7807	Intermediate Similarity	NPC474046
0.7807	Intermediate Similarity	NPC179626
0.7807	Intermediate Similarity	NPC259306
0.7798	Intermediate Similarity	NPC469607
0.7798	Intermediate Similarity	NPC50535
0.7798	Intermediate Similarity	NPC475802
0.7788	Intermediate Similarity	NPC477437
0.7788	Intermediate Similarity	NPC9848
0.7788	Intermediate Similarity	NPC75167
0.7788	Intermediate Similarity	NPC272617
0.7788	Intermediate Similarity	NPC312017
0.7788	Intermediate Similarity	NPC477438
0.7788	Intermediate Similarity	NPC311592
0.7778	Intermediate Similarity	NPC478057
0.7778	Intermediate Similarity	NPC474166
0.7778	Intermediate Similarity	NPC472401
0.7778	Intermediate Similarity	NPC469985
0.7778	Intermediate Similarity	NPC159533
0.7778	Intermediate Similarity	NPC19239
0.7778	Intermediate Similarity	NPC99266
0.7768	Intermediate Similarity	NPC157476
0.7768	Intermediate Similarity	NPC475668
0.7768	Intermediate Similarity	NPC475480
0.7768	Intermediate Similarity	NPC472928
0.7768	Intermediate Similarity	NPC34315
0.7768	Intermediate Similarity	NPC473921
0.7768	Intermediate Similarity	NPC304180
0.7768	Intermediate Similarity	NPC179798
0.7767	Intermediate Similarity	NPC477436
0.7767	Intermediate Similarity	NPC199543
0.7767	Intermediate Similarity	NPC477435
0.7767	Intermediate Similarity	NPC115021
0.776	Intermediate Similarity	NPC15850
0.7759	Intermediate Similarity	NPC77689
0.7759	Intermediate Similarity	NPC473636
0.7757	Intermediate Similarity	NPC472924
0.7757	Intermediate Similarity	NPC242666
0.7757	Intermediate Similarity	NPC472643
0.7757	Intermediate Similarity	NPC207885
0.7757	Intermediate Similarity	NPC112613
0.775	Intermediate Similarity	NPC470780
0.7748	Intermediate Similarity	NPC273433
0.7748	Intermediate Similarity	NPC15218
0.7745	Intermediate Similarity	NPC48732

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 NPC284365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1712
0.2-0.3	3685
0.3-0.4	2218
0.4-0.5	864
0.5-0.6	301
0.6-0.7	175
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
0.7818	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5778	Approved
0.7596	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7434	Intermediate Similarity	NPD6373	Approved
0.7434	Intermediate Similarity	NPD6372	Approved
0.7407	Intermediate Similarity	NPD7638	Approved
0.7395	Intermediate Similarity	NPD6319	Approved
0.7355	Intermediate Similarity	NPD8328	Phase 3
0.7345	Intermediate Similarity	NPD6899	Approved
0.7345	Intermediate Similarity	NPD7320	Approved
0.7345	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD7983	Approved
0.7304	Intermediate Similarity	NPD6649	Approved
0.7304	Intermediate Similarity	NPD6650	Approved
0.7257	Intermediate Similarity	NPD5701	Approved
0.7257	Intermediate Similarity	NPD5697	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7241	Intermediate Similarity	NPD6882	Approved
0.7217	Intermediate Similarity	NPD7102	Approved
0.7217	Intermediate Similarity	NPD6883	Approved
0.7217	Intermediate Similarity	NPD7290	Approved
0.72	Intermediate Similarity	NPD7319	Approved
0.7193	Intermediate Similarity	NPD6686	Approved
0.719	Intermediate Similarity	NPD6921	Approved
0.717	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD7637	Suspended
0.7155	Intermediate Similarity	NPD8130	Phase 1
0.7155	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD6869	Approved
0.7155	Intermediate Similarity	NPD6847	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7115	Discovery
0.713	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.7107	Intermediate Similarity	NPD6054	Approved
0.7107	Intermediate Similarity	NPD6059	Approved
0.7103	Intermediate Similarity	NPD6399	Phase 3
0.7097	Intermediate Similarity	NPD6616	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD46	Approved
0.7075	Intermediate Similarity	NPD6698	Approved
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5211	Phase 2
0.7049	Intermediate Similarity	NPD8513	Phase 3
0.7049	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD8517	Approved
0.7049	Intermediate Similarity	NPD8516	Approved
0.7043	Intermediate Similarity	NPD6011	Approved
0.704	Intermediate Similarity	NPD7078	Approved
0.704	Intermediate Similarity	NPD8293	Discontinued
0.7037	Intermediate Similarity	NPD7748	Approved
0.7034	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6992	Remote Similarity	NPD6370	Approved
0.6984	Remote Similarity	NPD7736	Approved
0.6981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6101	Approved
0.696	Remote Similarity	NPD7507	Approved
0.6949	Remote Similarity	NPD6053	Discontinued
0.693	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD4634	Approved
0.6911	Remote Similarity	NPD6015	Approved
0.6911	Remote Similarity	NPD6016	Approved
0.6909	Remote Similarity	NPD7839	Suspended
0.6903	Remote Similarity	NPD7632	Discontinued
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.686	Remote Similarity	NPD6009	Approved
0.6855	Remote Similarity	NPD5988	Approved
0.6838	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5328	Approved
0.6818	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5695	Phase 3
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7604	Phase 2
0.678	Remote Similarity	NPD6371	Approved
0.6777	Remote Similarity	NPD6274	Approved
0.6774	Remote Similarity	NPD5983	Phase 2
0.6772	Remote Similarity	NPD8074	Phase 3
0.6759	Remote Similarity	NPD5785	Approved
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5222	Approved
0.6757	Remote Similarity	NPD5221	Approved
0.6757	Remote Similarity	NPD4697	Phase 3
0.6754	Remote Similarity	NPD5224	Approved
0.6754	Remote Similarity	NPD5226	Approved
0.6754	Remote Similarity	NPD5225	Approved
0.6754	Remote Similarity	NPD4633	Approved
0.6748	Remote Similarity	NPD7101	Approved
0.6748	Remote Similarity	NPD7100	Approved
0.6729	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD5737	Approved
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD4768	Approved
0.6698	Remote Similarity	NPD5786	Approved
0.6697	Remote Similarity	NPD6079	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD5173	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6692	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4786	Approved
0.664	Remote Similarity	NPD6909	Approved
0.664	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6637	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD3667	Approved
0.6635	Remote Similarity	NPD6435	Approved
0.6635	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4730	Approved
0.661	Remote Similarity	NPD4729	Approved
0.6604	Remote Similarity	NPD1694	Approved
0.6589	Remote Similarity	NPD6033	Approved
0.6585	Remote Similarity	NPD6317	Approved
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5282	Discontinued
0.6569	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4754	Approved
0.6545	Remote Similarity	NPD5693	Phase 1
0.6542	Remote Similarity	NPD7334	Approved
0.6542	Remote Similarity	NPD6409	Approved
0.6542	Remote Similarity	NPD7521	Approved
0.6542	Remote Similarity	NPD6684	Approved
0.6542	Remote Similarity	NPD5330	Approved
0.6542	Remote Similarity	NPD3618	Phase 1
0.6542	Remote Similarity	NPD7146	Approved
0.6532	Remote Similarity	NPD6314	Approved
0.6532	Remote Similarity	NPD6313	Approved
0.6532	Remote Similarity	NPD7328	Approved
0.6532	Remote Similarity	NPD7327	Approved
0.6514	Remote Similarity	NPD4753	Phase 2
0.65	Remote Similarity	NPD5251	Approved
0.65	Remote Similarity	NPD5247	Approved
0.65	Remote Similarity	NPD5250	Approved
0.65	Remote Similarity	NPD5249	Phase 3
0.65	Remote Similarity	NPD5248	Approved
0.6481	Remote Similarity	NPD3573	Approved
0.648	Remote Similarity	NPD7516	Approved
0.6476	Remote Similarity	NPD4270	Approved
0.6476	Remote Similarity	NPD4269	Approved
0.6475	Remote Similarity	NPD8133	Approved
0.6471	Remote Similarity	NPD5128	Approved
0.6442	Remote Similarity	NPD5368	Approved
0.6436	Remote Similarity	NPD8039	Approved
0.6435	Remote Similarity	NPD6648	Approved
0.6422	Remote Similarity	NPD6903	Approved
0.6422	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7154	Phase 3
0.6396	Remote Similarity	NPD8035	Phase 2
0.6396	Remote Similarity	NPD8034	Phase 2
0.6391	Remote Similarity	NPD6845	Suspended
0.6389	Remote Similarity	NPD5279	Phase 3
0.6389	Remote Similarity	NPD6098	Approved
0.6378	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8379	Approved
0.6378	Remote Similarity	NPD8378	Approved
0.6378	Remote Similarity	NPD8380	Approved
0.6378	Remote Similarity	NPD8335	Approved
0.6378	Remote Similarity	NPD8296	Approved
0.637	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6080	Approved
0.6355	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3133	Approved
0.6355	Remote Similarity	NPD3665	Phase 1
0.6355	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3666	Approved
0.6348	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4202	Approved
0.633	Remote Similarity	NPD4250	Approved
0.633	Remote Similarity	NPD4251	Approved
0.6311	Remote Similarity	NPD5217	Approved
0.6311	Remote Similarity	NPD5215	Approved
0.6311	Remote Similarity	NPD5216	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