NPASS Compound

Structure

CID303217 OpenBabel06191716112D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.4597 -3.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1483 -2.8162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1702 1.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6285 -0.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1275 -1.2960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3928 -1.5465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9702 0.9835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1275 0.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4865 0.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6161 -0.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1928 -2.5215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3928 0.9835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7090 -0.3316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4876 -0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4905 0.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4876 0.2815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9702 -1.5465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4905 -1.2960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8506 -0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.5630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1140 -2.0778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.0630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0975 -0.1865 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 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 8 1 1 0 0 0 16 24 1 0 0 0 0 17 11 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 6 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	348.149
LogP:	4.628
LogD:	3.747
LogS:	-4.435
# Rotatable Bonds:	1
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	6.186
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.744
MDCK Permeability:	2.1456420654430985e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.401
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.706
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	96.99213409423828%
Volume Distribution (VD):	1.172
Pgp-substrate:	3.0613605976104736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.393
CYP1A2-substrate:	0.779
CYP2C19-inhibitor:	0.134
CYP2C19-substrate:	0.672
CYP2C9-inhibitor:	0.441
CYP2C9-substrate:	0.305
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.491
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	8.732
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.308
Skin Sensitization:	0.066
Carcinogencity:	0.928
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.534

Download Data

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

Natural Product: NPC303217

Natural Product ID:	NPC303217
*Common Name:**	Bipinnatin J
IUPAC Name:	n.a.
Synonyms:	Bipinnatin J
Standard InCHIKey:	RCFMTOJVVOOMTO-PVUOXGCVSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-11(2)17-6-5-14-10-16(24-20(14)22)8-12(3)7-15-9-13(4)19(23-15)18(17)21/h7,9-10,16-18,21H,1,5-6,8H2,2-4H3/b12-7-/t16-,17-,18-/m0/s1
SMILES:	C/C/1=C/c2cc(c(o2)[C@@H](O)[C@@H](CCC2=C[C@H](C1)OC2=O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401906
PubChem CID:	5470115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33566	Pseudopterogorgia bipinnata	Species	Gorgoniidae	Eukaryota	n.a.	San Andrs Island, Colombia	1996-MAY	PMID[10514303]
NPO40854	Gorgonian pseudopterogorgia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18271559]
NPO24654	Curculigo crassifolia	Species	Hypoxidaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18958422]
NPO25544	Encyclia michuacana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO24562	Saussurea petrovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24654	Curculigo crassifolia	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25544	Encyclia michuacana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24562	Saussurea petrovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3843	Rhododendron metternichii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25930	Cystoseira balearica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26421	Urtica laetevirens	Species	Urticaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	230.0	nM	PMID[534434]

☑ 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 NPC303217 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	272
0.1-0.2	1127
0.2-0.3	3255
0.3-0.4	7844
0.4-0.5	11056
0.5-0.6	6301
0.6-0.7	10423
0.7-0.8	2333
0.8-0.85	60
0.85-0.9	24
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC107571
0.9058	High Similarity	NPC254198
0.8865	High Similarity	NPC104924
0.8759	High Similarity	NPC474219
0.8759	High Similarity	NPC474378
0.8712	High Similarity	NPC474830
0.8702	High Similarity	NPC474829
0.8667	High Similarity	NPC97740
0.8652	High Similarity	NPC22248
0.8652	High Similarity	NPC110305
0.8647	High Similarity	NPC474438
0.8647	High Similarity	NPC474279
0.8636	High Similarity	NPC81912
0.8636	High Similarity	NPC329922
0.8636	High Similarity	NPC329694
0.8636	High Similarity	NPC474260
0.8623	High Similarity	NPC215109
0.8623	High Similarity	NPC170604
0.8613	High Similarity	NPC159786
0.8593	High Similarity	NPC17681
0.8592	High Similarity	NPC261733
0.8592	High Similarity	NPC307346
0.8592	High Similarity	NPC267004
0.8592	High Similarity	NPC218712
0.8571	High Similarity	NPC476016
0.8571	High Similarity	NPC282973
0.8561	High Similarity	NPC75557
0.8561	High Similarity	NPC71274
0.8531	High Similarity	NPC195920
0.8531	High Similarity	NPC37488
0.8529	High Similarity	NPC45358
0.8489	Intermediate Similarity	NPC473268
0.8433	Intermediate Similarity	NPC473355
0.8433	Intermediate Similarity	NPC471573
0.8433	Intermediate Similarity	NPC471554
0.8433	Intermediate Similarity	NPC471501
0.8409	Intermediate Similarity	NPC475818
0.8409	Intermediate Similarity	NPC476351
0.8369	Intermediate Similarity	NPC474615
0.8346	Intermediate Similarity	NPC118853
0.8345	Intermediate Similarity	NPC475864
0.8333	Intermediate Similarity	NPC289911
0.8333	Intermediate Similarity	NPC283284
0.8321	Intermediate Similarity	NPC136340
0.8288	Intermediate Similarity	NPC474317
0.8284	Intermediate Similarity	NPC471559
0.8261	Intermediate Similarity	NPC473982
0.8258	Intermediate Similarity	NPC474136
0.8255	Intermediate Similarity	NPC294511
0.8255	Intermediate Similarity	NPC121615
0.8231	Intermediate Similarity	NPC474255
0.8231	Intermediate Similarity	NPC471618
0.8231	Intermediate Similarity	NPC474220
0.8214	Intermediate Similarity	NPC14650
0.8195	Intermediate Similarity	NPC272487
0.8194	Intermediate Similarity	NPC184053
0.8182	Intermediate Similarity	NPC474817
0.8176	Intermediate Similarity	NPC474270
0.8176	Intermediate Similarity	NPC475904
0.8168	Intermediate Similarity	NPC187547
0.8168	Intermediate Similarity	NPC21831
0.8162	Intermediate Similarity	NPC137570
0.8143	Intermediate Similarity	NPC288209
0.8143	Intermediate Similarity	NPC106247
0.8129	Intermediate Similarity	NPC473344
0.8129	Intermediate Similarity	NPC471544
0.8129	Intermediate Similarity	NPC471545
0.8129	Intermediate Similarity	NPC261184
0.8121	Intermediate Similarity	NPC228842
0.8106	Intermediate Similarity	NPC473969
0.8106	Intermediate Similarity	NPC244293
0.8105	Intermediate Similarity	NPC84349
0.8099	Intermediate Similarity	NPC71638
0.8099	Intermediate Similarity	NPC64230
0.8082	Intermediate Similarity	NPC137295
0.8071	Intermediate Similarity	NPC474426
0.8071	Intermediate Similarity	NPC474425
0.8071	Intermediate Similarity	NPC474407
0.8056	Intermediate Similarity	NPC148374
0.8039	Intermediate Similarity	NPC194499
0.8015	Intermediate Similarity	NPC221798
0.8	Intermediate Similarity	NPC104854
0.8	Intermediate Similarity	NPC475044
0.8	Intermediate Similarity	NPC470976
0.8	Intermediate Similarity	NPC248795
0.8	Intermediate Similarity	NPC196979
0.8	Intermediate Similarity	NPC475063
0.8	Intermediate Similarity	NPC470977
0.7972	Intermediate Similarity	NPC286130
0.7971	Intermediate Similarity	NPC329707
0.7959	Intermediate Similarity	NPC473090
0.7956	Intermediate Similarity	NPC52035
0.7955	Intermediate Similarity	NPC208906
0.7955	Intermediate Similarity	NPC144745
0.7955	Intermediate Similarity	NPC131801
0.7949	Intermediate Similarity	NPC283209
0.7941	Intermediate Similarity	NPC243269
0.7931	Intermediate Similarity	NPC475045
0.7929	Intermediate Similarity	NPC183348
0.7929	Intermediate Similarity	NPC282230
0.7926	Intermediate Similarity	NPC471549
0.7926	Intermediate Similarity	NPC473379
0.7922	Intermediate Similarity	NPC88007
0.7922	Intermediate Similarity	NPC7059
0.7919	Intermediate Similarity	NPC71821
0.7908	Intermediate Similarity	NPC301233
0.7905	Intermediate Similarity	NPC10302
0.7905	Intermediate Similarity	NPC105381
0.7905	Intermediate Similarity	NPC213900
0.7905	Intermediate Similarity	NPC469642
0.7905	Intermediate Similarity	NPC247221
0.7899	Intermediate Similarity	NPC475236
0.7895	Intermediate Similarity	NPC246164
0.7895	Intermediate Similarity	NPC471613
0.7885	Intermediate Similarity	NPC18986
0.7885	Intermediate Similarity	NPC79571
0.7881	Intermediate Similarity	NPC88886
0.7881	Intermediate Similarity	NPC104172
0.7881	Intermediate Similarity	NPC212257
0.7879	Intermediate Similarity	NPC328451
0.7872	Intermediate Similarity	NPC15083
0.7871	Intermediate Similarity	NPC116639
0.7868	Intermediate Similarity	NPC291189
0.7868	Intermediate Similarity	NPC69403
0.7867	Intermediate Similarity	NPC66991
0.7862	Intermediate Similarity	NPC475028
0.7862	Intermediate Similarity	NPC474943
0.7862	Intermediate Similarity	NPC90953
0.7862	Intermediate Similarity	NPC475005
0.7862	Intermediate Similarity	NPC476025
0.7857	Intermediate Similarity	NPC939
0.7857	Intermediate Similarity	NPC66246
0.7857	Intermediate Similarity	NPC170546
0.7848	Intermediate Similarity	NPC475779
0.7834	Intermediate Similarity	NPC285567
0.7821	Intermediate Similarity	NPC8389
0.7821	Intermediate Similarity	NPC287559
0.782	Intermediate Similarity	NPC217180
0.782	Intermediate Similarity	NPC227660
0.782	Intermediate Similarity	NPC312525
0.781	Intermediate Similarity	NPC65735
0.781	Intermediate Similarity	NPC188377
0.7808	Intermediate Similarity	NPC473983
0.7808	Intermediate Similarity	NPC201370
0.7806	Intermediate Similarity	NPC304692
0.7806	Intermediate Similarity	NPC195954
0.7803	Intermediate Similarity	NPC205523
0.78	Intermediate Similarity	NPC286038
0.7792	Intermediate Similarity	NPC84721
0.7792	Intermediate Similarity	NPC75310
0.7786	Intermediate Similarity	NPC2596
0.7785	Intermediate Similarity	NPC469683
0.7778	Intermediate Similarity	NPC204592
0.7778	Intermediate Similarity	NPC44577
0.7771	Intermediate Similarity	NPC68848
0.7771	Intermediate Similarity	NPC169
0.777	Intermediate Similarity	NPC242756
0.777	Intermediate Similarity	NPC474476
0.777	Intermediate Similarity	NPC110211
0.777	Intermediate Similarity	NPC171870
0.7762	Intermediate Similarity	NPC19719
0.7762	Intermediate Similarity	NPC477280
0.7762	Intermediate Similarity	NPC477281
0.7756	Intermediate Similarity	NPC472779
0.7755	Intermediate Similarity	NPC477537
0.7754	Intermediate Similarity	NPC246166
0.7748	Intermediate Similarity	NPC14875
0.7748	Intermediate Similarity	NPC472969
0.7748	Intermediate Similarity	NPC469425
0.7748	Intermediate Similarity	NPC98009
0.7742	Intermediate Similarity	NPC104736
0.7742	Intermediate Similarity	NPC474542
0.7742	Intermediate Similarity	NPC469485
0.774	Intermediate Similarity	NPC202260
0.7736	Intermediate Similarity	NPC121995
0.7733	Intermediate Similarity	NPC291153
0.7733	Intermediate Similarity	NPC316535
0.7727	Intermediate Similarity	NPC60211
0.7727	Intermediate Similarity	NPC256141
0.7727	Intermediate Similarity	NPC114880
0.7724	Intermediate Similarity	NPC294470
0.7724	Intermediate Similarity	NPC186626
0.7722	Intermediate Similarity	NPC14822
0.7722	Intermediate Similarity	NPC288602
0.7722	Intermediate Similarity	NPC88841
0.7718	Intermediate Similarity	NPC476310
0.7718	Intermediate Similarity	NPC469615
0.7718	Intermediate Similarity	NPC476164
0.7712	Intermediate Similarity	NPC470908
0.7712	Intermediate Similarity	NPC243891
0.771	Intermediate Similarity	NPC1811
0.771	Intermediate Similarity	NPC26157
0.7707	Intermediate Similarity	NPC477402
0.7704	Intermediate Similarity	NPC4898
0.7703	Intermediate Similarity	NPC263337
0.7702	Intermediate Similarity	NPC476459
0.7698	Intermediate Similarity	NPC470858
0.7698	Intermediate Similarity	NPC216810
0.7697	Intermediate Similarity	NPC161955
0.7697	Intermediate Similarity	NPC215711

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 NPC303217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	865
0.2-0.3	1826
0.3-0.4	2568
0.4-0.5	2114
0.5-0.6	1070
0.6-0.7	402
0.7-0.8	55
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
0.8194	Intermediate Similarity	NPD4628	Phase 3
0.7687	Intermediate Similarity	NPD9092	Discovery
0.7677	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6799	Approved
0.7643	Intermediate Similarity	NPD7075	Discontinued
0.7639	Intermediate Similarity	NPD6355	Discontinued
0.7635	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6801	Discontinued
0.7518	Intermediate Similarity	NPD5647	Approved
0.7516	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD6599	Discontinued
0.7469	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6798	Discontinued
0.7417	Intermediate Similarity	NPD2354	Approved
0.7417	Intermediate Similarity	NPD3887	Approved
0.741	Intermediate Similarity	NPD6764	Approved
0.741	Intermediate Similarity	NPD6765	Approved
0.7386	Intermediate Similarity	NPD5401	Approved
0.7383	Intermediate Similarity	NPD6004	Phase 3
0.7383	Intermediate Similarity	NPD6002	Phase 3
0.7383	Intermediate Similarity	NPD6005	Phase 3
0.7383	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9545	Approved
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7357	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD2344	Approved
0.7267	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4062	Phase 3
0.726	Intermediate Similarity	NPD6233	Phase 2
0.725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD2799	Discontinued
0.7235	Intermediate Similarity	NPD6784	Approved
0.7235	Intermediate Similarity	NPD6785	Approved
0.7234	Intermediate Similarity	NPD9717	Approved
0.723	Intermediate Similarity	NPD6653	Approved
0.7205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD3817	Phase 2
0.7171	Intermediate Similarity	NPD1243	Approved
0.7169	Intermediate Similarity	NPD2163	Approved
0.7161	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD919	Approved
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6273	Approved
0.7107	Intermediate Similarity	NPD7411	Suspended
0.7105	Intermediate Similarity	NPD1549	Phase 2
0.7105	Intermediate Similarity	NPD5958	Discontinued
0.7101	Intermediate Similarity	NPD6559	Discontinued
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD2797	Approved
0.7078	Intermediate Similarity	NPD2309	Approved
0.7075	Intermediate Similarity	NPD2313	Discontinued
0.7075	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD920	Approved
0.7066	Intermediate Similarity	NPD3818	Discontinued
0.7063	Intermediate Similarity	NPD1934	Approved
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7048	Intermediate Similarity	NPD6166	Phase 2
0.7048	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD447	Suspended
0.7047	Intermediate Similarity	NPD230	Phase 1
0.7039	Intermediate Similarity	NPD1471	Phase 3
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4308	Phase 3
0.7019	Intermediate Similarity	NPD5761	Phase 2
0.7019	Intermediate Similarity	NPD7819	Suspended
0.7019	Intermediate Similarity	NPD5760	Phase 2
0.7019	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3750	Approved
0.7013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7006	Intermediate Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD3749	Approved
0.6993	Remote Similarity	NPD4534	Discontinued
0.6993	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD9494	Approved
0.6981	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4060	Phase 1
0.6974	Remote Similarity	NPD1551	Phase 2
0.6966	Remote Similarity	NPD1203	Approved
0.6966	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2067	Discontinued
0.6962	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3764	Approved
0.6957	Remote Similarity	NPD2629	Approved
0.6943	Remote Similarity	NPD2532	Approved
0.6943	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2533	Approved
0.6943	Remote Similarity	NPD2534	Approved
0.6936	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5844	Phase 1
0.6918	Remote Similarity	NPD2798	Approved
0.6912	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1510	Phase 2
0.6903	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4110	Phase 3
0.6901	Remote Similarity	NPD1778	Approved
0.6894	Remote Similarity	NPD958	Approved
0.6892	Remote Similarity	NPD7095	Approved
0.6889	Remote Similarity	NPD2684	Approved
0.6886	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3972	Approved
0.6875	Remote Similarity	NPD3226	Approved
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7199	Phase 2
0.6867	Remote Similarity	NPD1240	Approved
0.6863	Remote Similarity	NPD2935	Discontinued
0.686	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6190	Approved
0.6853	Remote Similarity	NPD3496	Discontinued
0.6849	Remote Similarity	NPD3266	Approved
0.6849	Remote Similarity	NPD3267	Approved
0.6849	Remote Similarity	NPD6362	Approved
0.6846	Remote Similarity	NPD411	Approved
0.6842	Remote Similarity	NPD6797	Phase 2
0.6835	Remote Similarity	NPD4662	Approved
0.6835	Remote Similarity	NPD4661	Approved
0.6821	Remote Similarity	NPD4340	Discontinued
0.6818	Remote Similarity	NPD2346	Discontinued
0.6815	Remote Similarity	NPD1358	Approved
0.6812	Remote Similarity	NPD7843	Approved
0.681	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2801	Approved
0.6807	Remote Similarity	NPD5494	Approved
0.6803	Remote Similarity	NPD1019	Discontinued
0.6802	Remote Similarity	NPD7251	Discontinued
0.6797	Remote Similarity	NPD3748	Approved
0.6792	Remote Similarity	NPD1512	Approved
0.6786	Remote Similarity	NPD3926	Phase 2
0.6786	Remote Similarity	NPD7157	Approved
0.6784	Remote Similarity	NPD7074	Phase 3
0.6781	Remote Similarity	NPD1876	Approved
0.6779	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1607	Approved
0.6774	Remote Similarity	NPD2424	Discontinued
0.6766	Remote Similarity	NPD8127	Discontinued
0.6766	Remote Similarity	NPD1247	Approved
0.6765	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7808	Phase 3
0.6761	Remote Similarity	NPD1894	Discontinued
0.6755	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3140	Approved
0.6755	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD3142	Approved
0.6753	Remote Similarity	NPD2240	Approved
0.6753	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2239	Approved
0.6746	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3134	Approved
0.6738	Remote Similarity	NPD9493	Approved
0.6735	Remote Similarity	NPD987	Approved
0.6731	Remote Similarity	NPD2800	Approved
0.673	Remote Similarity	NPD3146	Approved
0.673	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7768	Phase 2
0.6727	Remote Similarity	NPD4966	Approved
0.6727	Remote Similarity	NPD4965	Approved
0.6727	Remote Similarity	NPD4967	Phase 2
0.6726	Remote Similarity	NPD6808	Phase 2
0.6725	Remote Similarity	NPD7054	Approved
0.6724	Remote Similarity	NPD8313	Approved
0.6724	Remote Similarity	NPD8312	Approved
0.6711	Remote Similarity	NPD1933	Approved
0.6711	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7440	Discontinued
0.6708	Remote Similarity	NPD957	Approved
0.6705	Remote Similarity	NPD7685	Pre-registration
0.6691	Remote Similarity	NPD290	Approved
0.6691	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7003	Approved
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD2651	Approved
0.6667	Remote Similarity	NPD2649	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD2897	Discontinued
0.6648	Remote Similarity	NPD7879	Clinical (unspecified phase)

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