NPASS Compound

Structure

CID137430 OpenBabel06191715492D 31 33 0 0 1 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3267 -1.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6900 -0.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9246 -2.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0230 1.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4057 0.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6088 0.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0364 1.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6035 -0.1377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0812 -1.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9332 -2.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 1.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9903 0.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4142 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 1.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7071 -0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7071 -0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4142 1.0000 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 -3.4639 -2.6854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5505 -3.3482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0665 0.0275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3244 2.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0898 -1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3244 -1.6310 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 23 1 0 0 0 0 6 23 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 31 1 0 0 0 0 15 10 1 1 0 0 0 15 20 1 0 0 0 0 15 23 1 0 0 0 0 16 27 1 1 0 0 0 17 28 2 0 0 0 0 18 20 1 0 0 0 0 18 24 1 6 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 24 1 1 0 0 0 22 31 1 0 0 0 0 24 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	446.34
LogP:	2.301
LogD:	2.603
LogS:	-3.787
# Rotatable Bonds:	4
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	5.489
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.883
MDCK Permeability:	6.22506850049831e-05
Pgp-inhibitor:	0.745
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.321
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.285
Plasma Protein Binding (PPB):	61.53974914550781%
Volume Distribution (VD):	0.716
Pgp-substrate:	39.14603805541992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.322
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.243
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.21
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	3.513
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.654
Drug-inuced Liver Injury (DILI):	0.725
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.094
Carcinogencity:	0.258
Eye Corrosion:	0.006
Eye Irritation:	0.02
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC137430

Natural Product ID:	NPC137430
*Common Name:**	WABUTQVFTQIDOH-YCPIXCPXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WABUTQVFTQIDOH-YCPIXCPXSA-N
Standard InCHI:	InChI=1S/C24H34O7/c1-11-16(27)8-9-24(7)18(11)20(29)15-10-17(28)12(2)19(23(15,5)6)21(30-13(3)25)22(24)31-14(4)26/h15-16,18,20-22,27,29H,1,8-10H2,2-7H3/t15-,16-,18-,20+,21+,22-,24+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H](OC(=O)C)C2=C(C)C(=O)C[C@H](C2(C)C)[C@H]([C@H]2[C@@]1(C)CC[C@@H](C2=C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL129309
PubChem CID:	10455595
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	4

Activity Type	# Activity
Cell Line	1
Others	5

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[551909]
NPT2	Others	Unspecified		Control	=	139.0	%	PMID[551909]
NPT2	Others	Unspecified		Control	=	271.0	%	PMID[551909]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[551909]
NPT2	Others	Unspecified		Control	=	139.0	%	PMID[551910]
NPT2	Others	Unspecified		Control	=	271.0	%	PMID[551910]

☑ 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 NPC137430 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	219
0.1-0.2	1297
0.2-0.3	3947
0.3-0.4	7001
0.4-0.5	14514
0.5-0.6	7467
0.6-0.7	6634
0.7-0.8	1551
0.8-0.85	37
0.85-0.9	19
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC8196
0.9895	High Similarity	NPC99266
0.9684	High Similarity	NPC97435
0.9592	High Similarity	NPC143609
0.9495	High Similarity	NPC151393
0.949	High Similarity	NPC111952
0.8947	High Similarity	NPC99653
0.8922	High Similarity	NPC472439
0.8922	High Similarity	NPC469916
0.8854	High Similarity	NPC472416
0.8854	High Similarity	NPC472360
0.8842	High Similarity	NPC124374
0.8737	High Similarity	NPC48732
0.8737	High Similarity	NPC220216
0.8725	High Similarity	NPC472389
0.8713	High Similarity	NPC159533
0.8673	High Similarity	NPC471765
0.8673	High Similarity	NPC211810
0.8673	High Similarity	NPC221801
0.8673	High Similarity	NPC284194
0.8667	High Similarity	NPC317107
0.8641	High Similarity	NPC67321
0.8641	High Similarity	NPC187435
0.8641	High Similarity	NPC112780
0.8632	High Similarity	NPC261320
0.8614	High Similarity	NPC469606
0.8614	High Similarity	NPC31058
0.8614	High Similarity	NPC295791
0.8614	High Similarity	NPC273005
0.8585	High Similarity	NPC317687
0.8571	High Similarity	NPC471786
0.8571	High Similarity	NPC37603
0.8558	High Similarity	NPC322903
0.8542	High Similarity	NPC232202
0.8485	Intermediate Similarity	NPC202833
0.8438	Intermediate Similarity	NPC246028
0.8431	Intermediate Similarity	NPC476081
0.8431	Intermediate Similarity	NPC165250
0.8421	Intermediate Similarity	NPC471779
0.8411	Intermediate Similarity	NPC236217
0.8381	Intermediate Similarity	NPC476479
0.8381	Intermediate Similarity	NPC275539
0.8381	Intermediate Similarity	NPC189075
0.8381	Intermediate Similarity	NPC306265
0.8365	Intermediate Similarity	NPC469607
0.835	Intermediate Similarity	NPC478057
0.835	Intermediate Similarity	NPC471208
0.835	Intermediate Similarity	NPC95899
0.8333	Intermediate Similarity	NPC303559
0.8333	Intermediate Similarity	NPC471204
0.8333	Intermediate Similarity	NPC69713
0.8318	Intermediate Similarity	NPC188738
0.8318	Intermediate Similarity	NPC324683
0.8317	Intermediate Similarity	NPC222303
0.8317	Intermediate Similarity	NPC23364
0.8317	Intermediate Similarity	NPC216478
0.8317	Intermediate Similarity	NPC478056
0.8302	Intermediate Similarity	NPC273433
0.8302	Intermediate Similarity	NPC475586
0.8288	Intermediate Similarity	NPC475041
0.8286	Intermediate Similarity	NPC230541
0.8286	Intermediate Similarity	NPC110496
0.8283	Intermediate Similarity	NPC250075
0.8283	Intermediate Similarity	NPC105375
0.8283	Intermediate Similarity	NPC182826
0.8269	Intermediate Similarity	NPC146731
0.8269	Intermediate Similarity	NPC118911
0.8269	Intermediate Similarity	NPC296950
0.8241	Intermediate Similarity	NPC476801
0.8241	Intermediate Similarity	NPC269530
0.8235	Intermediate Similarity	NPC47024
0.8235	Intermediate Similarity	NPC476274
0.8229	Intermediate Similarity	NPC102640
0.8224	Intermediate Similarity	NPC5103
0.8218	Intermediate Similarity	NPC474343
0.8218	Intermediate Similarity	NPC175351
0.8218	Intermediate Similarity	NPC254496
0.8218	Intermediate Similarity	NPC224356
0.8218	Intermediate Similarity	NPC320306
0.8218	Intermediate Similarity	NPC132753
0.8218	Intermediate Similarity	NPC121402
0.8218	Intermediate Similarity	NPC473244
0.8218	Intermediate Similarity	NPC151681
0.8208	Intermediate Similarity	NPC325054
0.8208	Intermediate Similarity	NPC476802
0.8208	Intermediate Similarity	NPC89171
0.82	Intermediate Similarity	NPC183012
0.819	Intermediate Similarity	NPC102352
0.819	Intermediate Similarity	NPC127609
0.8182	Intermediate Similarity	NPC234858
0.8182	Intermediate Similarity	NPC154363
0.8182	Intermediate Similarity	NPC471127
0.8182	Intermediate Similarity	NPC199543
0.8173	Intermediate Similarity	NPC120321
0.8165	Intermediate Similarity	NPC469496
0.8165	Intermediate Similarity	NPC25909
0.8165	Intermediate Similarity	NPC469454
0.8165	Intermediate Similarity	NPC469463
0.8163	Intermediate Similarity	NPC158488
0.8155	Intermediate Similarity	NPC224720
0.8155	Intermediate Similarity	NPC476240
0.8155	Intermediate Similarity	NPC476223
0.8155	Intermediate Similarity	NPC115862
0.8155	Intermediate Similarity	NPC471412
0.8142	Intermediate Similarity	NPC67569
0.8137	Intermediate Similarity	NPC316598
0.8131	Intermediate Similarity	NPC141350
0.8125	Intermediate Similarity	NPC102996
0.8125	Intermediate Similarity	NPC473226
0.8119	Intermediate Similarity	NPC234993
0.8119	Intermediate Similarity	NPC472362
0.8119	Intermediate Similarity	NPC134072
0.8119	Intermediate Similarity	NPC472363
0.8119	Intermediate Similarity	NPC154526
0.8119	Intermediate Similarity	NPC7124
0.8119	Intermediate Similarity	NPC129569
0.8113	Intermediate Similarity	NPC144854
0.8113	Intermediate Similarity	NPC3316
0.8108	Intermediate Similarity	NPC473968
0.8108	Intermediate Similarity	NPC469684
0.8108	Intermediate Similarity	NPC10721
0.81	Intermediate Similarity	NPC57117
0.81	Intermediate Similarity	NPC196227
0.8095	Intermediate Similarity	NPC258532
0.8091	Intermediate Similarity	NPC474181
0.8081	Intermediate Similarity	NPC186363
0.8081	Intermediate Similarity	NPC473944
0.8081	Intermediate Similarity	NPC477574
0.8081	Intermediate Similarity	NPC233345
0.8081	Intermediate Similarity	NPC116726
0.8077	Intermediate Similarity	NPC136289
0.8077	Intermediate Similarity	NPC162973
0.8077	Intermediate Similarity	NPC472552
0.8077	Intermediate Similarity	NPC80781
0.8073	Intermediate Similarity	NPC472002
0.8073	Intermediate Similarity	NPC194951
0.8073	Intermediate Similarity	NPC12046
0.807	Intermediate Similarity	NPC23786
0.807	Intermediate Similarity	NPC269642
0.807	Intermediate Similarity	NPC470265
0.8061	Intermediate Similarity	NPC5509
0.8058	Intermediate Similarity	NPC471413
0.8058	Intermediate Similarity	NPC476767
0.8058	Intermediate Similarity	NPC54705
0.8058	Intermediate Similarity	NPC38855
0.8058	Intermediate Similarity	NPC307954
0.8058	Intermediate Similarity	NPC251680
0.8058	Intermediate Similarity	NPC327431
0.8058	Intermediate Similarity	NPC472644
0.8056	Intermediate Similarity	NPC469917
0.8056	Intermediate Similarity	NPC472417
0.8056	Intermediate Similarity	NPC478211
0.8056	Intermediate Similarity	NPC235014
0.8053	Intermediate Similarity	NPC48692
0.8041	Intermediate Similarity	NPC312561
0.8039	Intermediate Similarity	NPC474395
0.8039	Intermediate Similarity	NPC170131
0.8039	Intermediate Similarity	NPC70145
0.8039	Intermediate Similarity	NPC253826
0.8039	Intermediate Similarity	NPC285513
0.8039	Intermediate Similarity	NPC91695
0.8037	Intermediate Similarity	NPC277017
0.8037	Intermediate Similarity	NPC88701
0.8037	Intermediate Similarity	NPC154608
0.8037	Intermediate Similarity	NPC192813
0.8036	Intermediate Similarity	NPC475913
0.8021	Intermediate Similarity	NPC35933
0.802	Intermediate Similarity	NPC134067
0.802	Intermediate Similarity	NPC157686
0.802	Intermediate Similarity	NPC53565
0.802	Intermediate Similarity	NPC259042
0.8019	Intermediate Similarity	NPC323834
0.8019	Intermediate Similarity	NPC34768
0.8018	Intermediate Similarity	NPC176840
0.8	Intermediate Similarity	NPC69171
0.8	Intermediate Similarity	NPC475657
0.8	Intermediate Similarity	NPC53555
0.8	Intermediate Similarity	NPC962
0.8	Intermediate Similarity	NPC36688
0.8	Intermediate Similarity	NPC157441
0.8	Intermediate Similarity	NPC250109
0.8	Intermediate Similarity	NPC474165
0.8	Intermediate Similarity	NPC472757
0.8	Intermediate Similarity	NPC469789
0.8	Intermediate Similarity	NPC254202
0.7982	Intermediate Similarity	NPC179798
0.7982	Intermediate Similarity	NPC469655
0.7982	Intermediate Similarity	NPC100329
0.7982	Intermediate Similarity	NPC97939
0.7982	Intermediate Similarity	NPC475668
0.7982	Intermediate Similarity	NPC474846
0.7982	Intermediate Similarity	NPC247031
0.7982	Intermediate Similarity	NPC304180
0.7982	Intermediate Similarity	NPC475480
0.7982	Intermediate Similarity	NPC132790
0.7982	Intermediate Similarity	NPC469656
0.7982	Intermediate Similarity	NPC473921
0.7981	Intermediate Similarity	NPC207885
0.7981	Intermediate Similarity	NPC472643
0.7981	Intermediate Similarity	NPC472554

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 NPC137430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1687
0.2-0.3	3511
0.3-0.4	2354
0.4-0.5	923
0.5-0.6	311
0.6-0.7	156
0.7-0.8	14
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
0.8058	Intermediate Similarity	NPD7639	Approved
0.8058	Intermediate Similarity	NPD7640	Approved
0.7961	Intermediate Similarity	NPD7638	Approved
0.7798	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4225	Approved
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6686	Approved
0.7692	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7624	Intermediate Similarity	NPD46	Approved
0.7624	Intermediate Similarity	NPD6698	Approved
0.7573	Intermediate Similarity	NPD7748	Approved
0.757	Intermediate Similarity	NPD7632	Discontinued
0.7549	Intermediate Similarity	NPD7515	Phase 2
0.7455	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6371	Approved
0.7404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7900	Approved
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5344	Discontinued
0.7308	Intermediate Similarity	NPD5778	Approved
0.7308	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD1694	Approved
0.7297	Intermediate Similarity	NPD6412	Phase 2
0.7232	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3618	Phase 1
0.7217	Intermediate Similarity	NPD4632	Approved
0.7207	Intermediate Similarity	NPD7128	Approved
0.7207	Intermediate Similarity	NPD5739	Approved
0.7207	Intermediate Similarity	NPD6675	Approved
0.7207	Intermediate Similarity	NPD6402	Approved
0.7207	Intermediate Similarity	NPD6008	Approved
0.7172	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6373	Approved
0.7168	Intermediate Similarity	NPD6372	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7115	Intermediate Similarity	NPD5785	Approved
0.7107	Intermediate Similarity	NPD8328	Phase 3
0.708	Intermediate Similarity	NPD6899	Approved
0.708	Intermediate Similarity	NPD6881	Approved
0.708	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6648	Approved
0.7059	Intermediate Similarity	NPD7521	Approved
0.7059	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD6684	Approved
0.7059	Intermediate Similarity	NPD5330	Approved
0.7059	Intermediate Similarity	NPD6409	Approved
0.7059	Intermediate Similarity	NPD7146	Approved
0.7043	Intermediate Similarity	NPD6650	Approved
0.7043	Intermediate Similarity	NPD6649	Approved
0.7037	Intermediate Similarity	NPD6083	Phase 2
0.7037	Intermediate Similarity	NPD6084	Phase 2
0.7034	Intermediate Similarity	NPD6009	Approved
0.703	Intermediate Similarity	NPD4786	Approved
0.7019	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD6319	Approved
0.6991	Remote Similarity	NPD5701	Approved
0.6991	Remote Similarity	NPD5697	Approved
0.6967	Remote Similarity	NPD7604	Phase 2
0.696	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD7290	Approved
0.6957	Remote Similarity	NPD6883	Approved
0.6957	Remote Similarity	NPD7102	Approved
0.6952	Remote Similarity	NPD7838	Discovery
0.6942	Remote Similarity	NPD5983	Phase 2
0.693	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6911	Remote Similarity	NPD7492	Approved
0.6897	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6617	Approved
0.6897	Remote Similarity	NPD8130	Phase 1
0.6897	Remote Similarity	NPD6847	Approved
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6079	Approved
0.6887	Remote Similarity	NPD8035	Phase 2
0.6887	Remote Similarity	NPD8034	Phase 2
0.6887	Remote Similarity	NPD7983	Approved
0.6887	Remote Similarity	NPD6411	Approved
0.687	Remote Similarity	NPD6012	Approved
0.687	Remote Similarity	NPD6014	Approved
0.687	Remote Similarity	NPD6013	Approved
0.6863	Remote Similarity	NPD3665	Phase 1
0.6863	Remote Similarity	NPD3133	Approved
0.6863	Remote Similarity	NPD3666	Approved
0.686	Remote Similarity	NPD6054	Approved
0.686	Remote Similarity	NPD6059	Approved
0.6855	Remote Similarity	NPD6616	Approved
0.6855	Remote Similarity	NPD6336	Discontinued
0.6852	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7260	Phase 2
0.6842	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6882	Approved
0.6833	Remote Similarity	NPD7328	Approved
0.6833	Remote Similarity	NPD7327	Approved
0.6822	Remote Similarity	NPD4202	Approved
0.6818	Remote Similarity	NPD5696	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8033	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.68	Remote Similarity	NPD8293	Discontinued
0.68	Remote Similarity	NPD7078	Approved
0.6789	Remote Similarity	NPD4697	Phase 3
0.6786	Remote Similarity	NPD5211	Phase 2
0.6777	Remote Similarity	NPD7516	Approved
0.6752	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6370	Approved
0.6746	Remote Similarity	NPD7736	Approved
0.6729	Remote Similarity	NPD5284	Approved
0.6729	Remote Similarity	NPD5693	Phase 1
0.6729	Remote Similarity	NPD5281	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6727	Remote Similarity	NPD4755	Approved
0.6721	Remote Similarity	NPD8377	Approved
0.6721	Remote Similarity	NPD8294	Approved
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6101	Approved
0.6697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5363	Approved
0.6634	Remote Similarity	NPD4695	Discontinued
0.6613	Remote Similarity	NPD5988	Approved
0.6607	Remote Similarity	NPD4700	Approved
0.6607	Remote Similarity	NPD5286	Approved
0.6607	Remote Similarity	NPD5285	Approved
0.6607	Remote Similarity	NPD4696	Approved
0.6606	Remote Similarity	NPD5282	Discontinued
0.6602	Remote Similarity	NPD6110	Phase 1
0.66	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5173	Approved
0.6571	Remote Similarity	NPD5279	Phase 3
0.6571	Remote Similarity	NPD4519	Discontinued
0.6571	Remote Similarity	NPD4623	Approved
0.6557	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD6673	Approved
0.6542	Remote Similarity	NPD4753	Phase 2
0.6542	Remote Similarity	NPD6080	Approved
0.6542	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD3668	Phase 3
0.6535	Remote Similarity	NPD8074	Phase 3
0.6532	Remote Similarity	NPD6921	Approved
0.6529	Remote Similarity	NPD6274	Approved
0.6529	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6505	Remote Similarity	NPD4270	Approved
0.6505	Remote Similarity	NPD4269	Approved
0.6504	Remote Similarity	NPD7100	Approved
0.6504	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD5226	Approved
0.6491	Remote Similarity	NPD5225	Approved
0.6491	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD4633	Approved
0.6484	Remote Similarity	NPD6033	Approved
0.6475	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD8039	Approved
0.6442	Remote Similarity	NPD7154	Phase 3
0.6442	Remote Similarity	NPD5362	Discontinued
0.6435	Remote Similarity	NPD4754	Approved
0.6435	Remote Similarity	NPD5174	Approved
0.6435	Remote Similarity	NPD5175	Approved
0.6423	Remote Similarity	NPD6313	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD6050	Approved
0.6415	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5786	Approved
0.64	Remote Similarity	NPD6909	Approved
0.64	Remote Similarity	NPD6908	Approved
0.64	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5210	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