NPASS Compound

Structure

NPC161638 OpenBabel07101718322D 31 33 0 0 1 0 0 0 0 0999 V2000 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 1.0981 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 1.7321 -3.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 0.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 23 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 25 2 0 0 0 0 14 31 1 0 0 0 0 15 19 1 0 0 0 0 15 26 2 0 0 0 0 16 22 1 1 0 0 0 16 24 1 0 0 0 0 17 22 1 1 0 0 0 17 23 1 0 0 0 0 18 24 1 6 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 3 1 1 0 0 0 23 4 1 6 0 0 0 24 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	446.34
LogP:	2.478
LogD:	2.301
LogS:	-4.595
# Rotatable Bonds:	6
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	4.52
Fsp3:	0.75
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:	-4.944
MDCK Permeability:	2.542187758081127e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	75.4704360961914%
Volume Distribution (VD):	0.365
Pgp-substrate:	28.08316421508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.661
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.197
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.563

ADMET: Excretion

Clearance (CL):	4.684
Half-life (T1/2):	0.491

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.396
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.899
Carcinogencity:	0.057
Eye Corrosion:	0.055
Eye Irritation:	0.333
Respiratory Toxicity:	0.412

Download Data

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

Natural Product: NPC161638

Natural Product ID:	NPC161638
*Common Name:**	Jaspiferoic Acid A Dimethyl Ester
IUPAC Name:	methyl (3Z,3aS,5aR,6R,7R,9aR,9bR)-7-acetyloxy-3-(1-methoxy-1-oxopropan-2-ylidene)-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms:	Jaspiferoic Acid A Dimethyl Ester
Standard InCHIKey:	KLEWOBKRIMWWDD-MDSBSRMISA-N
Standard InCHI:	InChI=1S/C24H34O7/c1-13(20(27)29-6)19-15(26)12-17-22(3)11-9-18(31-14(2)25)24(5,21(28)30-7)16(22)8-10-23(17,19)4/h16-18H,8-12H2,1-7H3/b19-13+/t16-,17-,18-,22+,23+,24-/m1/s1
SMILES:	C/C(=C1/C(=O)C[C@@H]2[C@@]3(C)CC[C@H]([C@@](C)([C@@H]3CC[C@]12C)C(=O)OC)OC(=O)C)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497903
PubChem CID:	44583729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	3.3	ug.mL-1	PMID[450181]

☑ 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 NPC161638 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	229
0.1-0.2	1464
0.2-0.3	5077
0.3-0.4	10654
0.4-0.5	10891
0.5-0.6	6660
0.6-0.7	5692
0.7-0.8	1918
0.8-0.85	93
0.85-0.9	16
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC2049
0.9302	High Similarity	NPC80335
0.8913	High Similarity	NPC110937
0.8842	High Similarity	NPC473283
0.8842	High Similarity	NPC329345
0.8842	High Similarity	NPC475526
0.8791	High Similarity	NPC473435
0.8791	High Similarity	NPC473280
0.8791	High Similarity	NPC473431
0.8791	High Similarity	NPC471078
0.8667	High Similarity	NPC8062
0.8602	High Similarity	NPC106425
0.8602	High Similarity	NPC151725
0.8602	High Similarity	NPC122324
0.8587	High Similarity	NPC84893
0.8587	High Similarity	NPC470697
0.8542	High Similarity	NPC155332
0.8542	High Similarity	NPC320447
0.8542	High Similarity	NPC32577
0.8542	High Similarity	NPC114540
0.8488	Intermediate Similarity	NPC282293
0.8485	Intermediate Similarity	NPC318363
0.8485	Intermediate Similarity	NPC473482
0.8485	Intermediate Similarity	NPC475418
0.8462	Intermediate Similarity	NPC474842
0.8462	Intermediate Similarity	NPC475965
0.8454	Intermediate Similarity	NPC72151
0.8438	Intermediate Similarity	NPC168319
0.8438	Intermediate Similarity	NPC194028
0.8421	Intermediate Similarity	NPC108368
0.8421	Intermediate Similarity	NPC252295
0.8421	Intermediate Similarity	NPC57079
0.8404	Intermediate Similarity	NPC242848
0.8404	Intermediate Similarity	NPC471153
0.84	Intermediate Similarity	NPC475065
0.8384	Intermediate Similarity	NPC329048
0.8384	Intermediate Similarity	NPC330011
0.8333	Intermediate Similarity	NPC35751
0.8333	Intermediate Similarity	NPC117685
0.8316	Intermediate Similarity	NPC253826
0.8298	Intermediate Similarity	NPC88310
0.8283	Intermediate Similarity	NPC266570
0.828	Intermediate Similarity	NPC139692
0.8265	Intermediate Similarity	NPC180204
0.8265	Intermediate Similarity	NPC112009
0.8247	Intermediate Similarity	NPC282524
0.8247	Intermediate Similarity	NPC115899
0.8247	Intermediate Similarity	NPC93744
0.8247	Intermediate Similarity	NPC476888
0.8211	Intermediate Similarity	NPC307164
0.8211	Intermediate Similarity	NPC7124
0.82	Intermediate Similarity	NPC473284
0.8172	Intermediate Similarity	NPC473944
0.8163	Intermediate Similarity	NPC476890
0.8163	Intermediate Similarity	NPC40918
0.8155	Intermediate Similarity	NPC476163
0.8155	Intermediate Similarity	NPC69291
0.8155	Intermediate Similarity	NPC285956
0.8144	Intermediate Similarity	NPC266955
0.8144	Intermediate Similarity	NPC470906
0.8144	Intermediate Similarity	NPC477521
0.8144	Intermediate Similarity	NPC474012
0.8144	Intermediate Similarity	NPC476299
0.8144	Intermediate Similarity	NPC201406
0.8137	Intermediate Similarity	NPC470496
0.8137	Intermediate Similarity	NPC179642
0.8125	Intermediate Similarity	NPC38530
0.8125	Intermediate Similarity	NPC224356
0.8125	Intermediate Similarity	NPC84335
0.8125	Intermediate Similarity	NPC132753
0.8125	Intermediate Similarity	NPC151681
0.8125	Intermediate Similarity	NPC121402
0.8125	Intermediate Similarity	NPC175351
0.8111	Intermediate Similarity	NPC474013
0.8111	Intermediate Similarity	NPC189311
0.8105	Intermediate Similarity	NPC473648
0.8105	Intermediate Similarity	NPC33473
0.8085	Intermediate Similarity	NPC271652
0.8085	Intermediate Similarity	NPC79117
0.8081	Intermediate Similarity	NPC476889
0.8081	Intermediate Similarity	NPC475050
0.8077	Intermediate Similarity	NPC122056
0.8065	Intermediate Similarity	NPC51486
0.8061	Intermediate Similarity	NPC471075
0.8058	Intermediate Similarity	NPC474315
0.8058	Intermediate Similarity	NPC470960
0.8043	Intermediate Similarity	NPC93411
0.8041	Intermediate Similarity	NPC316598
0.8041	Intermediate Similarity	NPC471932
0.8041	Intermediate Similarity	NPC176845
0.8023	Intermediate Similarity	NPC471151
0.8023	Intermediate Similarity	NPC316500
0.8022	Intermediate Similarity	NPC220478
0.8022	Intermediate Similarity	NPC195640
0.8021	Intermediate Similarity	NPC472362
0.8021	Intermediate Similarity	NPC154526
0.8021	Intermediate Similarity	NPC250757
0.8021	Intermediate Similarity	NPC301534
0.8021	Intermediate Similarity	NPC327788
0.8021	Intermediate Similarity	NPC134072
0.8021	Intermediate Similarity	NPC17578
0.8021	Intermediate Similarity	NPC472363
0.8021	Intermediate Similarity	NPC234993
0.8021	Intermediate Similarity	NPC240673
0.8	Intermediate Similarity	NPC38830
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC184870
0.8	Intermediate Similarity	NPC120158
0.8	Intermediate Similarity	NPC189616
0.8	Intermediate Similarity	NPC147912
0.8	Intermediate Similarity	NPC471720
0.8	Intermediate Similarity	NPC67259
0.8	Intermediate Similarity	NPC475193
0.8	Intermediate Similarity	NPC284915
0.8	Intermediate Similarity	NPC124207
0.8	Intermediate Similarity	NPC474555
0.798	Intermediate Similarity	NPC80781
0.798	Intermediate Similarity	NPC165250
0.798	Intermediate Similarity	NPC476081
0.7979	Intermediate Similarity	NPC472814
0.7979	Intermediate Similarity	NPC177037
0.7979	Intermediate Similarity	NPC472953
0.7978	Intermediate Similarity	NPC200513
0.7959	Intermediate Similarity	NPC471413
0.7959	Intermediate Similarity	NPC476303
0.7959	Intermediate Similarity	NPC307954
0.7959	Intermediate Similarity	NPC251680
0.7957	Intermediate Similarity	NPC288699
0.7957	Intermediate Similarity	NPC174342
0.7957	Intermediate Similarity	NPC177141
0.7957	Intermediate Similarity	NPC471043
0.7957	Intermediate Similarity	NPC73995
0.7941	Intermediate Similarity	NPC90946
0.7941	Intermediate Similarity	NPC300614
0.7938	Intermediate Similarity	NPC23680
0.7938	Intermediate Similarity	NPC53844
0.7938	Intermediate Similarity	NPC26413
0.7938	Intermediate Similarity	NPC73911
0.7917	Intermediate Similarity	NPC476519
0.7912	Intermediate Similarity	NPC177932
0.7912	Intermediate Similarity	NPC323765
0.79	Intermediate Similarity	NPC476237
0.79	Intermediate Similarity	NPC176883
0.79	Intermediate Similarity	NPC120321
0.79	Intermediate Similarity	NPC476770
0.79	Intermediate Similarity	NPC471365
0.79	Intermediate Similarity	NPC159533
0.79	Intermediate Similarity	NPC470954
0.79	Intermediate Similarity	NPC36321
0.79	Intermediate Similarity	NPC471364
0.79	Intermediate Similarity	NPC324001
0.79	Intermediate Similarity	NPC132395
0.7895	Intermediate Similarity	NPC474185
0.7895	Intermediate Similarity	NPC115021
0.7895	Intermediate Similarity	NPC472871
0.7889	Intermediate Similarity	NPC470046
0.7889	Intermediate Similarity	NPC470047
0.7889	Intermediate Similarity	NPC193198
0.7879	Intermediate Similarity	NPC473514
0.7879	Intermediate Similarity	NPC471412
0.7879	Intermediate Similarity	NPC310981
0.7872	Intermediate Similarity	NPC152467
0.7872	Intermediate Similarity	NPC477149
0.7872	Intermediate Similarity	NPC477147
0.7872	Intermediate Similarity	NPC113393
0.7872	Intermediate Similarity	NPC78973
0.7872	Intermediate Similarity	NPC302280
0.7872	Intermediate Similarity	NPC471896
0.7864	Intermediate Similarity	NPC31522
0.7857	Intermediate Similarity	NPC98868
0.785	Intermediate Similarity	NPC243065
0.785	Intermediate Similarity	NPC20302
0.785	Intermediate Similarity	NPC140055
0.785	Intermediate Similarity	NPC286528
0.785	Intermediate Similarity	NPC55296
0.785	Intermediate Similarity	NPC167606
0.785	Intermediate Similarity	NPC470492
0.7849	Intermediate Similarity	NPC477128
0.7849	Intermediate Similarity	NPC104560
0.7849	Intermediate Similarity	NPC215831
0.7849	Intermediate Similarity	NPC226863
0.7849	Intermediate Similarity	NPC473879
0.7843	Intermediate Similarity	NPC475570
0.7843	Intermediate Similarity	NPC220974
0.7843	Intermediate Similarity	NPC91034
0.7841	Intermediate Similarity	NPC150646
0.7841	Intermediate Similarity	NPC469620
0.7835	Intermediate Similarity	NPC118159
0.7835	Intermediate Similarity	NPC476797
0.7835	Intermediate Similarity	NPC120708
0.7835	Intermediate Similarity	NPC98874
0.7826	Intermediate Similarity	NPC131813
0.7826	Intermediate Similarity	NPC470050
0.7826	Intermediate Similarity	NPC470051
0.7822	Intermediate Similarity	NPC476764
0.7822	Intermediate Similarity	NPC476763
0.7816	Intermediate Similarity	NPC189206
0.7812	Intermediate Similarity	NPC477130
0.7812	Intermediate Similarity	NPC474554
0.7812	Intermediate Similarity	NPC474690

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 NPC161638 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	1792
0.2-0.3	3892
0.3-0.4	2156
0.4-0.5	663
0.5-0.6	191
0.6-0.7	180
0.7-0.8	82
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8041	Intermediate Similarity	NPD7638	Approved
0.8022	Intermediate Similarity	NPD6684	Approved
0.8022	Intermediate Similarity	NPD7334	Approved
0.8022	Intermediate Similarity	NPD7146	Approved
0.8022	Intermediate Similarity	NPD7521	Approved
0.8022	Intermediate Similarity	NPD6409	Approved
0.8022	Intermediate Similarity	NPD5330	Approved
0.7978	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7640	Approved
0.7959	Intermediate Similarity	NPD7639	Approved
0.7912	Intermediate Similarity	NPD1694	Approved
0.785	Intermediate Similarity	NPD7115	Discovery
0.7849	Intermediate Similarity	NPD6903	Approved
0.7849	Intermediate Similarity	NPD6672	Approved
0.7849	Intermediate Similarity	NPD5737	Approved
0.7849	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7632	Discontinued
0.7677	Intermediate Similarity	NPD4225	Approved
0.7629	Intermediate Similarity	NPD7900	Approved
0.7629	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7748	Approved
0.7604	Intermediate Similarity	NPD5693	Phase 1
0.7573	Intermediate Similarity	NPD7128	Approved
0.7573	Intermediate Similarity	NPD5739	Approved
0.7573	Intermediate Similarity	NPD6675	Approved
0.7573	Intermediate Similarity	NPD6402	Approved
0.7551	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3618	Phase 1
0.7429	Intermediate Similarity	NPD6899	Approved
0.7429	Intermediate Similarity	NPD7320	Approved
0.7429	Intermediate Similarity	NPD6881	Approved
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD7902	Approved
0.74	Intermediate Similarity	NPD6084	Phase 2
0.7396	Intermediate Similarity	NPD6673	Approved
0.7396	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD5328	Approved
0.7396	Intermediate Similarity	NPD6080	Approved
0.7358	Intermediate Similarity	NPD6373	Approved
0.7358	Intermediate Similarity	NPD6372	Approved
0.7358	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5697	Approved
0.7333	Intermediate Similarity	NPD5701	Approved
0.729	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7102	Approved
0.729	Intermediate Similarity	NPD7290	Approved
0.729	Intermediate Similarity	NPD6883	Approved
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6079	Approved
0.7245	Intermediate Similarity	NPD8035	Phase 2
0.7245	Intermediate Similarity	NPD8034	Phase 2
0.7238	Intermediate Similarity	NPD6008	Approved
0.7222	Intermediate Similarity	NPD6847	Approved
0.7222	Intermediate Similarity	NPD6869	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7222	Intermediate Similarity	NPD8130	Phase 1
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6617	Approved
0.7216	Intermediate Similarity	NPD6051	Approved
0.72	Intermediate Similarity	NPD5695	Phase 3
0.7196	Intermediate Similarity	NPD6014	Approved
0.7196	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD6013	Approved
0.7188	Intermediate Similarity	NPD3573	Approved
0.7158	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5696	Approved
0.7156	Intermediate Similarity	NPD8297	Approved
0.7156	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.7113	Intermediate Similarity	NPD5208	Approved
0.7103	Intermediate Similarity	NPD6011	Approved
0.71	Intermediate Similarity	NPD6001	Approved
0.7083	Intermediate Similarity	NPD6098	Approved
0.7071	Intermediate Similarity	NPD6050	Approved
0.7064	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4755	Approved
0.7053	Intermediate Similarity	NPD3666	Approved
0.7053	Intermediate Similarity	NPD4786	Approved
0.7053	Intermediate Similarity	NPD3133	Approved
0.7053	Intermediate Similarity	NPD3665	Phase 1
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7045	Intermediate Similarity	NPD5777	Approved
0.7021	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD4202	Approved
0.6975	Remote Similarity	NPD7319	Approved
0.697	Remote Similarity	NPD5692	Phase 3
0.6961	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5222	Approved
0.6961	Remote Similarity	NPD5221	Approved
0.6961	Remote Similarity	NPD4697	Phase 3
0.6957	Remote Similarity	NPD3617	Approved
0.6952	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD5286	Approved
0.6923	Remote Similarity	NPD5285	Approved
0.6923	Remote Similarity	NPD4700	Approved
0.6923	Remote Similarity	NPD4696	Approved
0.6923	Remote Similarity	NPD6117	Approved
0.69	Remote Similarity	NPD5694	Approved
0.69	Remote Similarity	NPD7637	Suspended
0.6893	Remote Similarity	NPD5173	Approved
0.687	Remote Similarity	NPD6319	Approved
0.6869	Remote Similarity	NPD4753	Phase 2
0.6864	Remote Similarity	NPD7507	Approved
0.6848	Remote Similarity	NPD6116	Phase 1
0.6842	Remote Similarity	NPD5209	Approved
0.6822	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD6868	Approved
0.6814	Remote Similarity	NPD6274	Approved
0.68	Remote Similarity	NPD5207	Approved
0.6792	Remote Similarity	NPD5226	Approved
0.6792	Remote Similarity	NPD4633	Approved
0.6792	Remote Similarity	NPD5224	Approved
0.6792	Remote Similarity	NPD5225	Approved
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7100	Approved
0.6783	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD7492	Approved
0.6774	Remote Similarity	NPD6118	Approved
0.6774	Remote Similarity	NPD6114	Approved
0.6774	Remote Similarity	NPD6115	Approved
0.6774	Remote Similarity	NPD6697	Approved
0.6733	Remote Similarity	NPD6411	Approved
0.6729	Remote Similarity	NPD5174	Approved
0.6729	Remote Similarity	NPD5175	Approved
0.6724	Remote Similarity	NPD6054	Approved
0.6724	Remote Similarity	NPD6059	Approved
0.6723	Remote Similarity	NPD6616	Approved
0.6703	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5654	Approved
0.6699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5223	Approved
0.6697	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD4632	Approved
0.6633	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD5363	Approved
0.663	Remote Similarity	NPD8039	Approved
0.6629	Remote Similarity	NPD4137	Phase 3
0.6612	Remote Similarity	NPD7736	Approved
0.661	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6317	Approved
0.6606	Remote Similarity	NPD4768	Approved
0.6606	Remote Similarity	NPD4767	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4754	Approved
0.6574	Remote Similarity	NPD6052	Approved
0.6571	Remote Similarity	NPD5959	Approved
0.6569	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD5279	Phase 3
0.6556	Remote Similarity	NPD4691	Approved
0.6556	Remote Similarity	NPD4747	Approved
0.6552	Remote Similarity	NPD7328	Approved
0.6552	Remote Similarity	NPD6313	Approved
0.6552	Remote Similarity	NPD7327	Approved
0.6552	Remote Similarity	NPD6314	Approved
0.6549	Remote Similarity	NPD6053	Discontinued
0.6538	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD4629	Approved
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6531	Remote Similarity	NPD4197	Approved
0.6525	Remote Similarity	NPD6015	Approved
0.6525	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD7516	Approved
0.6495	Remote Similarity	NPD4269	Approved
0.6495	Remote Similarity	NPD4270	Approved
0.6486	Remote Similarity	NPD5128	Approved
0.6486	Remote Similarity	NPD4730	Approved
0.6486	Remote Similarity	NPD4729	Approved
0.6484	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7732	Phase 3
0.6471	Remote Similarity	NPD5988	Approved
0.6466	Remote Similarity	NPD6009	Approved
0.6458	Remote Similarity	NPD7525	Registered
0.6444	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8294	Approved
0.6441	Remote Similarity	NPD8377	Approved
0.6429	Remote Similarity	NPD4788	Approved
0.6417	Remote Similarity	NPD7604	Phase 2
0.6417	Remote Similarity	NPD8328	Phase 3
0.64	Remote Similarity	NPD4689	Approved
0.64	Remote Similarity	NPD4519	Discontinued

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