NPASS Compound

Structure

CID37488 OpenBabel06191715362D 31 34 0 0 1 0 0 0 0 0999 V2000 1.4535 -6.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2659 -6.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4874 -3.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7514 -0.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7494 -2.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7673 -4.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 -4.4260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0550 -2.2065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0173 -2.2210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7673 -0.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6541 -5.7733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2873 -4.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7746 -4.7806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5903 -1.3210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0550 -3.2065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0173 -3.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -4.0920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8235 -3.6774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 -1.7356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 -0.9871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8834 -3.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7553 -2.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7746 -0.6324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0359 -5.1015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8834 -4.6920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7158 -2.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7494 -3.1920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3388 -4.7551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5229 -1.5912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0628 -2.7065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 5 27 1 0 0 0 0 6 13 1 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 9 19 2 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 12 24 2 0 0 0 0 12 28 1 0 0 0 0 13 11 1 1 0 0 0 14 8 1 6 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 28 1 6 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 23 1 1 0 0 0 20 31 1 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 4 1 1 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.16
Volume:	424.005
LogP:	4.1
LogD:	2.705
LogS:	-4.79
# Rotatable Bonds:	5
TPSA:	111.64
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	6.25
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.773
MDCK Permeability:	4.3087260564789176e-05
Pgp-inhibitor:	0.129
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.499

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	93.65906524658203%
Volume Distribution (VD):	1.103
Pgp-substrate:	8.466132164001465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.212
CYP2C19-substrate:	0.335
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.297
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	3.111
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.135
Carcinogencity:	0.622
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC37488

Natural Product ID:	NPC37488
*Common Name:**	WJKBXPONHMNWTM-ODLNTGJHSA-N
IUPAC Name:	n.a.
Synonyms:	13Alpha-Acetoxypukalide
Standard InCHIKey:	WJKBXPONHMNWTM-ODLNTGJHSA-N
Standard InCHI:	InChI=1S/C23H26O8/c1-11(2)13-6-17(28-12(3)24)15-8-14(29-22(15)26)10-23(4)20(31-23)19-9-16(21(25)27-5)18(7-13)30-19/h8-9,13-14,17,20H,1,6-7,10H2,2-5H3/t13-,14-,17-,20-,23-/m1/s1
SMILES:	C=C(C)[C@@H]1C[C@H](C2=C[C@H](C[C@]3(C)[C@@H](c4cc(c(C1)o4)C(=O)OC)O3)OC2=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465178
PubChem CID:	44583999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO17857	Leptogorgia alba	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844963]
NPO32839	leptogorgia rigida	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844963]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17857	Leptogorgia alba	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19279	Cotylelobium melanoxylon	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18893	Delphinium gueneri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19063	Aconitum grossedentatum	Species	Ranunculaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	109000.0	nM	PMID[469497]

☑ 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 NPC37488 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	398
0.1-0.2	1573
0.2-0.3	4456
0.3-0.4	9277
0.4-0.5	9853
0.5-0.6	6718
0.6-0.7	8383
0.7-0.8	1987
0.8-0.85	20
0.85-0.9	10
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC474317
0.9712	High Similarity	NPC195920
0.9643	High Similarity	NPC475864
0.9568	High Similarity	NPC110305
0.9507	High Similarity	NPC474220
0.9507	High Similarity	NPC471618
0.9507	High Similarity	NPC474255
0.9441	High Similarity	NPC475904
0.9441	High Similarity	NPC474270
0.942	High Similarity	NPC474615
0.9353	High Similarity	NPC282973
0.9247	High Similarity	NPC474219
0.9247	High Similarity	NPC474378
0.9097	High Similarity	NPC104924
0.9021	High Similarity	NPC254198
0.8978	High Similarity	NPC136340
0.8881	High Similarity	NPC248795
0.8759	High Similarity	NPC22248
0.8741	High Similarity	NPC107571
0.8732	High Similarity	NPC286130
0.8723	High Similarity	NPC159786
0.8609	High Similarity	NPC470380
0.8531	High Similarity	NPC303217
0.8521	High Similarity	NPC200718
0.825	Intermediate Similarity	NPC473766
0.825	Intermediate Similarity	NPC473753
0.8239	Intermediate Similarity	NPC45947
0.82	Intermediate Similarity	NPC86935
0.8165	Intermediate Similarity	NPC333139
0.8138	Intermediate Similarity	NPC106247
0.8105	Intermediate Similarity	NPC19747
0.8101	Intermediate Similarity	NPC473368
0.8086	Intermediate Similarity	NPC472895
0.8079	Intermediate Similarity	NPC218712
0.8079	Intermediate Similarity	NPC267004
0.8079	Intermediate Similarity	NPC307346
0.8079	Intermediate Similarity	NPC261733
0.805	Intermediate Similarity	NPC305016
0.8038	Intermediate Similarity	NPC286722
0.8037	Intermediate Similarity	NPC302392
0.8028	Intermediate Similarity	NPC137570
0.8012	Intermediate Similarity	NPC261184
0.7987	Intermediate Similarity	NPC473473
0.7987	Intermediate Similarity	NPC475295
0.7987	Intermediate Similarity	NPC237155
0.7975	Intermediate Similarity	NPC126723
0.7975	Intermediate Similarity	NPC107646
0.7975	Intermediate Similarity	NPC278010
0.7975	Intermediate Similarity	NPC250769
0.7975	Intermediate Similarity	NPC209364
0.7975	Intermediate Similarity	NPC60973
0.7975	Intermediate Similarity	NPC263265
0.7975	Intermediate Similarity	NPC295608
0.7974	Intermediate Similarity	NPC62799
0.7973	Intermediate Similarity	NPC473268
0.7958	Intermediate Similarity	NPC216810
0.7949	Intermediate Similarity	NPC18135
0.7947	Intermediate Similarity	NPC473152
0.7945	Intermediate Similarity	NPC474425
0.7945	Intermediate Similarity	NPC474407
0.7945	Intermediate Similarity	NPC474426
0.7937	Intermediate Similarity	NPC25255
0.7937	Intermediate Similarity	NPC191828
0.7937	Intermediate Similarity	NPC475381
0.7922	Intermediate Similarity	NPC221809
0.7911	Intermediate Similarity	NPC131725
0.7908	Intermediate Similarity	NPC10302
0.7908	Intermediate Similarity	NPC105381
0.7901	Intermediate Similarity	NPC276735
0.7901	Intermediate Similarity	NPC123088
0.7888	Intermediate Similarity	NPC193798
0.7888	Intermediate Similarity	NPC117986
0.7888	Intermediate Similarity	NPC470939
0.7866	Intermediate Similarity	NPC323137
0.7862	Intermediate Similarity	NPC474542
0.7857	Intermediate Similarity	NPC294365
0.7857	Intermediate Similarity	NPC171656
0.7848	Intermediate Similarity	NPC288534
0.7848	Intermediate Similarity	NPC114880
0.7843	Intermediate Similarity	NPC84479
0.784	Intermediate Similarity	NPC469846
0.7834	Intermediate Similarity	NPC475717
0.7831	Intermediate Similarity	NPC144288
0.7829	Intermediate Similarity	NPC470856
0.7826	Intermediate Similarity	NPC472653
0.7821	Intermediate Similarity	NPC211625
0.7812	Intermediate Similarity	NPC470625
0.7805	Intermediate Similarity	NPC279768
0.7805	Intermediate Similarity	NPC179015
0.7805	Intermediate Similarity	NPC173149
0.7805	Intermediate Similarity	NPC476850
0.7805	Intermediate Similarity	NPC270312
0.7805	Intermediate Similarity	NPC476861
0.7799	Intermediate Similarity	NPC301233
0.7799	Intermediate Similarity	NPC75310
0.7792	Intermediate Similarity	NPC76657
0.7791	Intermediate Similarity	NPC476860
0.7791	Intermediate Similarity	NPC476858
0.7791	Intermediate Similarity	NPC476856
0.7791	Intermediate Similarity	NPC56358
0.7791	Intermediate Similarity	NPC476857
0.7785	Intermediate Similarity	NPC98028
0.7778	Intermediate Similarity	NPC188649
0.7778	Intermediate Similarity	NPC5079
0.7778	Intermediate Similarity	NPC184391
0.7778	Intermediate Similarity	NPC223415
0.7778	Intermediate Similarity	NPC80635
0.7771	Intermediate Similarity	NPC46551
0.7764	Intermediate Similarity	NPC116639
0.7764	Intermediate Similarity	NPC477403
0.7764	Intermediate Similarity	NPC476930
0.7756	Intermediate Similarity	NPC52106
0.7756	Intermediate Similarity	NPC473428
0.7756	Intermediate Similarity	NPC471285
0.7755	Intermediate Similarity	NPC473344
0.7755	Intermediate Similarity	NPC471545
0.7755	Intermediate Similarity	NPC471544
0.7755	Intermediate Similarity	NPC45358
0.775	Intermediate Similarity	NPC469485
0.7744	Intermediate Similarity	NPC23387
0.7744	Intermediate Similarity	NPC121995
0.7742	Intermediate Similarity	NPC213482
0.7742	Intermediate Similarity	NPC316535
0.774	Intermediate Similarity	NPC21460
0.7738	Intermediate Similarity	NPC167340
0.7736	Intermediate Similarity	NPC308555
0.773	Intermediate Similarity	NPC476035
0.773	Intermediate Similarity	NPC51568
0.773	Intermediate Similarity	NPC88841
0.773	Intermediate Similarity	NPC475039
0.773	Intermediate Similarity	NPC302369
0.773	Intermediate Similarity	NPC134254
0.773	Intermediate Similarity	NPC14822
0.773	Intermediate Similarity	NPC39986
0.773	Intermediate Similarity	NPC1848
0.773	Intermediate Similarity	NPC14499
0.773	Intermediate Similarity	NPC288602
0.773	Intermediate Similarity	NPC234660
0.773	Intermediate Similarity	NPC285567
0.7727	Intermediate Similarity	NPC476310
0.7727	Intermediate Similarity	NPC476164
0.7727	Intermediate Similarity	NPC137295
0.7725	Intermediate Similarity	NPC120220
0.7722	Intermediate Similarity	NPC191104
0.7716	Intermediate Similarity	NPC335761
0.7716	Intermediate Similarity	NPC287559
0.7714	Intermediate Similarity	NPC67345
0.7714	Intermediate Similarity	NPC244862
0.7708	Intermediate Similarity	NPC52035
0.7707	Intermediate Similarity	NPC329180
0.7703	Intermediate Similarity	NPC470859
0.7702	Intermediate Similarity	NPC81405
0.7702	Intermediate Similarity	NPC472283
0.7702	Intermediate Similarity	NPC173544
0.7702	Intermediate Similarity	NPC187149
0.7697	Intermediate Similarity	NPC476853
0.7697	Intermediate Similarity	NPC259007
0.7697	Intermediate Similarity	NPC329215
0.7697	Intermediate Similarity	NPC204088
0.7697	Intermediate Similarity	NPC473908
0.7697	Intermediate Similarity	NPC472651
0.7692	Intermediate Similarity	NPC224418
0.7692	Intermediate Similarity	NPC472665
0.7688	Intermediate Similarity	NPC214541
0.7688	Intermediate Similarity	NPC44675
0.7687	Intermediate Similarity	NPC17681
0.7679	Intermediate Similarity	NPC472584
0.7676	Intermediate Similarity	NPC323118
0.7673	Intermediate Similarity	NPC44577
0.7673	Intermediate Similarity	NPC75906
0.7673	Intermediate Similarity	NPC295650
0.7673	Intermediate Similarity	NPC475777
0.7669	Intermediate Similarity	NPC68848
0.7669	Intermediate Similarity	NPC239270
0.7669	Intermediate Similarity	NPC290400
0.7669	Intermediate Similarity	NPC197596
0.7669	Intermediate Similarity	NPC74749
0.7669	Intermediate Similarity	NPC43971
0.7669	Intermediate Similarity	NPC303210
0.7669	Intermediate Similarity	NPC95472
0.7669	Intermediate Similarity	NPC96443
0.7669	Intermediate Similarity	NPC49009
0.7669	Intermediate Similarity	NPC19554
0.7665	Intermediate Similarity	NPC294512
0.7665	Intermediate Similarity	NPC159232
0.7662	Intermediate Similarity	NPC205071
0.7662	Intermediate Similarity	NPC470741
0.7658	Intermediate Similarity	NPC164299
0.7658	Intermediate Similarity	NPC88445
0.7655	Intermediate Similarity	NPC476016
0.7654	Intermediate Similarity	NPC140952
0.7651	Intermediate Similarity	NPC67450
0.7651	Intermediate Similarity	NPC155264
0.7651	Intermediate Similarity	NPC193881
0.7651	Intermediate Similarity	NPC210460
0.7651	Intermediate Similarity	NPC472652
0.7651	Intermediate Similarity	NPC271235
0.764	Intermediate Similarity	NPC471746
0.764	Intermediate Similarity	NPC104736
0.764	Intermediate Similarity	NPC99381

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 NPC37488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	1044
0.2-0.3	2196
0.3-0.4	2739
0.4-0.5	1766
0.5-0.6	784
0.6-0.7	261
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8165	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6799	Approved
0.7578	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7075	Discontinued
0.7532	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7425	Intermediate Similarity	NPD3926	Phase 2
0.7423	Intermediate Similarity	NPD5402	Approved
0.7423	Intermediate Similarity	NPD3817	Phase 2
0.7421	Intermediate Similarity	NPD5403	Approved
0.7419	Intermediate Similarity	NPD1243	Approved
0.7414	Intermediate Similarity	NPD8434	Phase 2
0.7405	Intermediate Similarity	NPD5401	Approved
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD2796	Approved
0.7315	Intermediate Similarity	NPD6832	Phase 2
0.7305	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7246	Intermediate Similarity	NPD5494	Approved
0.7215	Intermediate Similarity	NPD3887	Approved
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7093	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD2344	Approved
0.707	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD6808	Phase 2
0.7048	Intermediate Similarity	NPD7819	Suspended
0.703	Intermediate Similarity	NPD7411	Suspended
0.7029	Intermediate Similarity	NPD6764	Approved
0.7029	Intermediate Similarity	NPD6765	Approved
0.7024	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3749	Approved
0.6994	Remote Similarity	NPD3818	Discontinued
0.6994	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.697	Remote Similarity	NPD4380	Phase 2
0.6968	Remote Similarity	NPD447	Suspended
0.6968	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2353	Approved
0.6962	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5761	Phase 2
0.6946	Remote Similarity	NPD5760	Phase 2
0.6943	Remote Similarity	NPD2799	Discontinued
0.6937	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6559	Discontinued
0.6928	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1549	Phase 2
0.6913	Remote Similarity	NPD9717	Approved
0.6909	Remote Similarity	NPD3226	Approved
0.6903	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2309	Approved
0.6893	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1934	Approved
0.6883	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6166	Phase 2
0.6879	Remote Similarity	NPD2067	Discontinued
0.6879	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2800	Approved
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6785	Approved
0.6872	Remote Similarity	NPD6784	Approved
0.6868	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6355	Discontinued
0.6859	Remote Similarity	NPD1933	Approved
0.6855	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7033	Discontinued
0.6824	Remote Similarity	NPD17	Approved
0.6813	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3751	Discontinued
0.6792	Remote Similarity	NPD1551	Phase 2
0.679	Remote Similarity	NPD2354	Approved
0.6786	Remote Similarity	NPD6279	Approved
0.6786	Remote Similarity	NPD6280	Approved
0.678	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6797	Phase 2
0.6768	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6002	Phase 3
0.675	Remote Similarity	NPD6005	Phase 3
0.675	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6004	Phase 3
0.6746	Remote Similarity	NPD2801	Approved
0.6743	Remote Similarity	NPD7473	Discontinued
0.6742	Remote Similarity	NPD7251	Discontinued
0.6732	Remote Similarity	NPD5647	Approved
0.6731	Remote Similarity	NPD6233	Phase 2
0.673	Remote Similarity	NPD3748	Approved
0.673	Remote Similarity	NPD1510	Phase 2
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5353	Approved
0.6704	Remote Similarity	NPD7808	Phase 3
0.6689	Remote Similarity	NPD1608	Approved
0.6688	Remote Similarity	NPD4307	Phase 2
0.6688	Remote Similarity	NPD1240	Approved
0.6687	Remote Similarity	NPD2935	Discontinued
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5953	Discontinued
0.6685	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2654	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8285	Discontinued
0.6646	Remote Similarity	NPD2346	Discontinued
0.6646	Remote Similarity	NPD230	Phase 1
0.6644	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7074	Phase 3
0.6627	Remote Similarity	NPD1512	Approved
0.6623	Remote Similarity	NPD2798	Approved
0.6622	Remote Similarity	NPD9092	Discovery
0.661	Remote Similarity	NPD2163	Approved
0.6604	Remote Similarity	NPD1607	Approved
0.6601	Remote Similarity	NPD1876	Approved
0.6597	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6190	Approved
0.6579	Remote Similarity	NPD3972	Approved
0.6577	Remote Similarity	NPD9545	Approved
0.6575	Remote Similarity	NPD1241	Discontinued
0.6575	Remote Similarity	NPD8312	Approved
0.6575	Remote Similarity	NPD8313	Approved
0.6573	Remote Similarity	NPD7054	Approved
0.657	Remote Similarity	NPD7768	Phase 2
0.6566	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3146	Approved
0.6566	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3268	Approved
0.6561	Remote Similarity	NPD411	Approved
0.6557	Remote Similarity	NPD8150	Discontinued
0.6556	Remote Similarity	NPD7685	Pre-registration
0.655	Remote Similarity	NPD7972	Discontinued
0.6536	Remote Similarity	NPD7472	Approved
0.6529	Remote Similarity	NPD6386	Approved
0.6529	Remote Similarity	NPD6385	Approved
0.6527	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3750	Approved
0.6524	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4308	Phase 3
0.6519	Remote Similarity	NPD4062	Phase 3
0.6514	Remote Similarity	NPD6959	Discontinued
0.651	Remote Similarity	NPD7435	Discontinued
0.6506	Remote Similarity	NPD1511	Approved
0.65	Remote Similarity	NPD6651	Approved
0.6497	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7286	Phase 2
0.648	Remote Similarity	NPD5844	Phase 1
0.6474	Remote Similarity	NPD4967	Phase 2
0.6474	Remote Similarity	NPD4966	Approved
0.6474	Remote Similarity	NPD4965	Approved
0.646	Remote Similarity	NPD7097	Phase 1
0.6458	Remote Similarity	NPD2182	Approved
0.6456	Remote Similarity	NPD3764	Approved
0.6456	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2797	Approved
0.645	Remote Similarity	NPD957	Approved
0.645	Remote Similarity	NPD8404	Phase 2
0.6443	Remote Similarity	NPD9493	Approved
0.6441	Remote Similarity	NPD5242	Approved
0.6433	Remote Similarity	NPD5889	Approved
0.6433	Remote Similarity	NPD5890	Approved
0.6429	Remote Similarity	NPD5049	Phase 3
0.6425	Remote Similarity	NPD7799	Discontinued
0.6424	Remote Similarity	NPD5585	Approved
0.642	Remote Similarity	NPD7199	Phase 2
0.6416	Remote Similarity	NPD2296	Approved
0.641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2424	Discontinued
0.6402	Remote Similarity	NPD5958	Discontinued
0.6402	Remote Similarity	NPD2897	Discontinued
0.64	Remote Similarity	NPD6234	Discontinued
0.6398	Remote Similarity	NPD6653	Approved
0.6395	Remote Similarity	NPD37	Approved
0.6389	Remote Similarity	NPD1358	Approved
0.6384	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5711	Approved
0.6384	Remote Similarity	NPD5710	Approved
0.638	Remote Similarity	NPD2438	Suspended
0.6375	Remote Similarity	NPD3142	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