NPASS Compound

Structure

NPC470297 OpenBabel07101718292D 31 32 0 0 1 0 0 0 0 0999 V2000 0.7725 -4.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8968 -3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0561 -1.8256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7092 -4.6992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2745 -3.0769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5255 -2.1402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9602 -3.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6796 -0.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8398 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 -0.9697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8398 0.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3591 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.4545 0.0000 C 0 0 1 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 -1.6796 2.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 -1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 -1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 9 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 7 30 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 25 1 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 27 2 0 0 0 0 16 28 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 20 26 1 0 0 0 0 21 31 1 1 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 26 1 1 0 0 0 23 30 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 25 6 1 6 0 0 0 26 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.27
Volume:	469.272
LogP:	3.499
LogD:	3.52
LogS:	-4.343
# Rotatable Bonds:	10
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	5.322
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.668
MDCK Permeability:	2.431091525068041e-05
Pgp-inhibitor:	0.2
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	64.03158569335938%
Volume Distribution (VD):	2.231
Pgp-substrate:	36.48787307739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.594
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	5.874
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.427
Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.973
Carcinogencity:	0.394
Eye Corrosion:	0.802
Eye Irritation:	0.132
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC470297

Natural Product ID:	NPC470297
*Common Name:**	[(2R,4As,5S,7R,8R,8As)-4,4A-Diformyl-5-Methoxy-7,8-Dimethyl-8-[(2E)-3-Methylpenta-2,4-Dienyl]-1,2,5,6,7,8A-Hexahydronaphthalen-2-Yl] 2-Methylbutanoate
IUPAC Name:	[(2R,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-methoxy-7,8-dimethyl-8-[(2E)-3-methylpenta-2,4-dienyl]-1,2,5,6,7,8a-hexahydronaphthalen-2-yl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	IIENMWMYMSMVQK-BDLHYKASSA-N
Standard InCHI:	InChI=1S/C26H38O5/c1-8-17(3)10-11-25(6)19(5)12-23(30-7)26(16-28)20(15-27)13-21(14-22(25)26)31-24(29)18(4)9-2/h8,10,13,15-16,18-19,21-23H,1,9,11-12,14H2,2-7H3/b17-10+/t18?,19-,21+,22+,23+,25-,26+/m1/s1
SMILES:	CCC(C)C(=O)OC1CC2C(C(CC(C2(C(=C1)C=O)C=O)OC)C)(C)CC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL194808
PubChem CID:	44404751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO1241	Laetia procera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16168652]
NPO1241	Laetia procera	Species	Salicaceae	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
Others	6

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	9.6	uM	PMID[496471]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	2.7	n.a.	PMID[496471]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	6.04	uM	PMID[496471]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	3.79	uM	PMID[496471]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	30.3	uM	PMID[496471]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	50.9	uM	PMID[496471]

☑ 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 NPC470297 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	257
0.1-0.2	1299
0.2-0.3	3960
0.3-0.4	7631
0.4-0.5	13095
0.5-0.6	9546
0.6-0.7	5654
0.7-0.8	1230
0.8-0.85	19
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC89171
0.95	High Similarity	NPC476802
0.9135	High Similarity	NPC476801
0.8673	High Similarity	NPC470697
0.8544	High Similarity	NPC254202
0.8485	Intermediate Similarity	NPC477130
0.8485	Intermediate Similarity	NPC477129
0.8476	Intermediate Similarity	NPC133422
0.8431	Intermediate Similarity	NPC476933
0.8381	Intermediate Similarity	NPC469607
0.8381	Intermediate Similarity	NPC1679
0.83	Intermediate Similarity	NPC38830
0.83	Intermediate Similarity	NPC269729
0.8288	Intermediate Similarity	NPC474518
0.8286	Intermediate Similarity	NPC189616
0.8283	Intermediate Similarity	NPC473944
0.8265	Intermediate Similarity	NPC284561
0.8257	Intermediate Similarity	NPC277769
0.8252	Intermediate Similarity	NPC475385
0.8252	Intermediate Similarity	NPC475392
0.8252	Intermediate Similarity	NPC471413
0.8252	Intermediate Similarity	NPC475202
0.8235	Intermediate Similarity	NPC2049
0.8224	Intermediate Similarity	NPC275539
0.8224	Intermediate Similarity	NPC189075
0.8218	Intermediate Similarity	NPC274417
0.82	Intermediate Similarity	NPC475657
0.819	Intermediate Similarity	NPC95585
0.819	Intermediate Similarity	NPC282233
0.8182	Intermediate Similarity	NPC152467
0.8182	Intermediate Similarity	NPC56448
0.8182	Intermediate Similarity	NPC471204
0.8173	Intermediate Similarity	NPC471412
0.8155	Intermediate Similarity	NPC23364
0.8148	Intermediate Similarity	NPC474243
0.8148	Intermediate Similarity	NPC112457
0.8144	Intermediate Similarity	NPC220478
0.8137	Intermediate Similarity	NPC151725
0.8137	Intermediate Similarity	NPC106425
0.8137	Intermediate Similarity	NPC122324
0.8131	Intermediate Similarity	NPC110496
0.8125	Intermediate Similarity	NPC476959
0.8108	Intermediate Similarity	NPC238667
0.8095	Intermediate Similarity	NPC469606
0.8095	Intermediate Similarity	NPC162973
0.8095	Intermediate Similarity	NPC31058
0.8095	Intermediate Similarity	NPC273005
0.8091	Intermediate Similarity	NPC269530
0.8091	Intermediate Similarity	NPC4573
0.8091	Intermediate Similarity	NPC90952
0.8081	Intermediate Similarity	NPC73995
0.8077	Intermediate Similarity	NPC174314
0.807	Intermediate Similarity	NPC476962
0.8058	Intermediate Similarity	NPC38530
0.8058	Intermediate Similarity	NPC84335
0.8058	Intermediate Similarity	NPC110937
0.8053	Intermediate Similarity	NPC470420
0.8053	Intermediate Similarity	NPC284707
0.8039	Intermediate Similarity	NPC183012
0.8036	Intermediate Similarity	NPC477509
0.8019	Intermediate Similarity	NPC95899
0.8019	Intermediate Similarity	NPC471365
0.8019	Intermediate Similarity	NPC471364
0.8019	Intermediate Similarity	NPC120321
0.8019	Intermediate Similarity	NPC132395
0.8018	Intermediate Similarity	NPC469454
0.8018	Intermediate Similarity	NPC469463
0.8018	Intermediate Similarity	NPC469496
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC328141
0.8	Intermediate Similarity	NPC310981
0.8	Intermediate Similarity	NPC304180
0.8	Intermediate Similarity	NPC212679
0.8	Intermediate Similarity	NPC220454
0.8	Intermediate Similarity	NPC159748
0.8	Intermediate Similarity	NPC179798
0.8	Intermediate Similarity	NPC101651
0.7982	Intermediate Similarity	NPC469370
0.7982	Intermediate Similarity	NPC475520
0.7981	Intermediate Similarity	NPC264378
0.7981	Intermediate Similarity	NPC471932
0.798	Intermediate Similarity	NPC477128
0.798	Intermediate Similarity	NPC215831
0.7965	Intermediate Similarity	NPC98249
0.7965	Intermediate Similarity	NPC134430
0.7965	Intermediate Similarity	NPC53396
0.7963	Intermediate Similarity	NPC476958
0.7963	Intermediate Similarity	NPC179380
0.7961	Intermediate Similarity	NPC118159
0.7961	Intermediate Similarity	NPC29952
0.7944	Intermediate Similarity	NPC118911
0.7941	Intermediate Similarity	NPC471446
0.7941	Intermediate Similarity	NPC474841
0.7941	Intermediate Similarity	NPC473434
0.7941	Intermediate Similarity	NPC250075
0.7928	Intermediate Similarity	NPC12046
0.7928	Intermediate Similarity	NPC265391
0.7928	Intermediate Similarity	NPC194951
0.7925	Intermediate Similarity	NPC475091
0.7917	Intermediate Similarity	NPC470813
0.7909	Intermediate Similarity	NPC253906
0.7909	Intermediate Similarity	NPC478209
0.7905	Intermediate Similarity	NPC470761
0.7905	Intermediate Similarity	NPC35751
0.7905	Intermediate Similarity	NPC474012
0.7905	Intermediate Similarity	NPC476299
0.7905	Intermediate Similarity	NPC470906
0.7905	Intermediate Similarity	NPC473219
0.7905	Intermediate Similarity	NPC54705
0.7895	Intermediate Similarity	NPC21326
0.7895	Intermediate Similarity	NPC473720
0.789	Intermediate Similarity	NPC476479
0.7879	Intermediate Similarity	NPC175293
0.7876	Intermediate Similarity	NPC476963
0.787	Intermediate Similarity	NPC478208
0.7863	Intermediate Similarity	NPC55602
0.7857	Intermediate Similarity	NPC25909
0.7857	Intermediate Similarity	NPC470120
0.7857	Intermediate Similarity	NPC157441
0.7857	Intermediate Similarity	NPC159333
0.785	Intermediate Similarity	NPC473283
0.785	Intermediate Similarity	NPC475526
0.785	Intermediate Similarity	NPC329345
0.7843	Intermediate Similarity	NPC79117
0.7843	Intermediate Similarity	NPC474185
0.7838	Intermediate Similarity	NPC474315
0.7838	Intermediate Similarity	NPC188738
0.7838	Intermediate Similarity	NPC470960
0.783	Intermediate Similarity	NPC168319
0.783	Intermediate Similarity	NPC111292
0.783	Intermediate Similarity	NPC472637
0.783	Intermediate Similarity	NPC194028
0.783	Intermediate Similarity	NPC476478
0.7826	Intermediate Similarity	NPC476960
0.7826	Intermediate Similarity	NPC473636
0.7826	Intermediate Similarity	NPC77689
0.7822	Intermediate Similarity	NPC469372
0.7822	Intermediate Similarity	NPC474842
0.7822	Intermediate Similarity	NPC475965
0.781	Intermediate Similarity	NPC316598
0.781	Intermediate Similarity	NPC176845
0.781	Intermediate Similarity	NPC57079
0.781	Intermediate Similarity	NPC216478
0.781	Intermediate Similarity	NPC108368
0.7807	Intermediate Similarity	NPC475809
0.7807	Intermediate Similarity	NPC469684
0.7807	Intermediate Similarity	NPC23046
0.78	Intermediate Similarity	NPC473229
0.78	Intermediate Similarity	NPC226863
0.7798	Intermediate Similarity	NPC302788
0.7788	Intermediate Similarity	NPC470953
0.7788	Intermediate Similarity	NPC202833
0.7788	Intermediate Similarity	NPC311166
0.7778	Intermediate Similarity	NPC476001
0.7778	Intermediate Similarity	NPC96268
0.7778	Intermediate Similarity	NPC168248
0.7778	Intermediate Similarity	NPC474898
0.7778	Intermediate Similarity	NPC146731
0.7778	Intermediate Similarity	NPC170538
0.7778	Intermediate Similarity	NPC239162
0.7768	Intermediate Similarity	NPC69291
0.7767	Intermediate Similarity	NPC473435
0.7767	Intermediate Similarity	NPC471078
0.7767	Intermediate Similarity	NPC473280
0.7767	Intermediate Similarity	NPC473431
0.7759	Intermediate Similarity	NPC476961
0.7759	Intermediate Similarity	NPC184555
0.7757	Intermediate Similarity	NPC155332
0.7757	Intermediate Similarity	NPC164551
0.7757	Intermediate Similarity	NPC114540
0.7757	Intermediate Similarity	NPC32577
0.7757	Intermediate Similarity	NPC80781
0.7757	Intermediate Similarity	NPC137430
0.7757	Intermediate Similarity	NPC320447
0.7757	Intermediate Similarity	NPC478156
0.7757	Intermediate Similarity	NPC476081
0.7757	Intermediate Similarity	NPC235369
0.7748	Intermediate Similarity	NPC286880
0.7748	Intermediate Similarity	NPC5103
0.7745	Intermediate Similarity	NPC477574
0.7736	Intermediate Similarity	NPC117685
0.7736	Intermediate Similarity	NPC473204
0.7736	Intermediate Similarity	NPC104861
0.7736	Intermediate Similarity	NPC306856
0.7736	Intermediate Similarity	NPC471041
0.7736	Intermediate Similarity	NPC47024
0.7727	Intermediate Similarity	NPC318363
0.7727	Intermediate Similarity	NPC475418
0.7727	Intermediate Similarity	NPC322903
0.7727	Intermediate Similarity	NPC151393
0.7727	Intermediate Similarity	NPC306265
0.7727	Intermediate Similarity	NPC473482
0.7727	Intermediate Similarity	NPC473483
0.7719	Intermediate Similarity	NPC72772
0.7719	Intermediate Similarity	NPC469794
0.7714	Intermediate Similarity	NPC474343
0.7714	Intermediate Similarity	NPC226986
0.7714	Intermediate Similarity	NPC476768
0.7714	Intermediate Similarity	NPC292133
0.7714	Intermediate Similarity	NPC472188

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 NPC470297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	1509
0.2-0.3	3515
0.3-0.4	2389
0.4-0.5	1025
0.5-0.6	316
0.6-0.7	158
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7677	Intermediate Similarity	NPD1694	Approved
0.767	Intermediate Similarity	NPD5778	Approved
0.767	Intermediate Similarity	NPD5779	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7429	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7900	Approved
0.7407	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD7639	Approved
0.7404	Intermediate Similarity	NPD6411	Approved
0.7387	Intermediate Similarity	NPD6008	Approved
0.7374	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3573	Approved
0.735	Intermediate Similarity	NPD7115	Discovery
0.7315	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD7902	Approved
0.7212	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6101	Approved
0.7168	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7748	Approved
0.7069	Intermediate Similarity	NPD6650	Approved
0.7069	Intermediate Similarity	NPD6649	Approved
0.701	Intermediate Similarity	NPD8039	Approved
0.7009	Intermediate Similarity	NPD6399	Phase 3
0.6984	Remote Similarity	NPD7319	Approved
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4697	Phase 3
0.6957	Remote Similarity	NPD6881	Approved
0.6957	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD6648	Approved
0.6923	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD7521	Approved
0.6923	Remote Similarity	NPD6409	Approved
0.6923	Remote Similarity	NPD7146	Approved
0.6923	Remote Similarity	NPD6684	Approved
0.6923	Remote Similarity	NPD7334	Approved
0.6916	Remote Similarity	NPD6079	Approved
0.6916	Remote Similarity	NPD7515	Phase 2
0.6897	Remote Similarity	NPD6372	Approved
0.6897	Remote Similarity	NPD6373	Approved
0.6885	Remote Similarity	NPD6319	Approved
0.6881	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7507	Approved
0.6875	Remote Similarity	NPD7260	Phase 2
0.687	Remote Similarity	NPD5697	Approved
0.6863	Remote Similarity	NPD5209	Approved
0.6838	Remote Similarity	NPD7290	Approved
0.6838	Remote Similarity	NPD7102	Approved
0.6838	Remote Similarity	NPD6883	Approved
0.6829	Remote Similarity	NPD8517	Approved
0.6829	Remote Similarity	NPD8516	Approved
0.6829	Remote Similarity	NPD8513	Phase 3
0.6829	Remote Similarity	NPD8515	Approved
0.6822	Remote Similarity	NPD5785	Approved
0.6814	Remote Similarity	NPD7632	Discontinued
0.681	Remote Similarity	NPD6011	Approved
0.681	Remote Similarity	NPD6686	Approved
0.6807	Remote Similarity	NPD4632	Approved
0.68	Remote Similarity	NPD7492	Approved
0.6792	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6903	Approved
0.6792	Remote Similarity	NPD5737	Approved
0.6792	Remote Similarity	NPD6672	Approved
0.6783	Remote Similarity	NPD5739	Approved
0.6783	Remote Similarity	NPD6675	Approved
0.6783	Remote Similarity	NPD6402	Approved
0.6783	Remote Similarity	NPD7128	Approved
0.678	Remote Similarity	NPD6847	Approved
0.678	Remote Similarity	NPD6869	Approved
0.678	Remote Similarity	NPD8130	Phase 1
0.678	Remote Similarity	NPD6617	Approved
0.6759	Remote Similarity	NPD7637	Suspended
0.6759	Remote Similarity	NPD7983	Approved
0.6752	Remote Similarity	NPD6014	Approved
0.6752	Remote Similarity	NPD6013	Approved
0.6752	Remote Similarity	NPD6012	Approved
0.6752	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6054	Approved
0.6746	Remote Similarity	NPD6616	Approved
0.6729	Remote Similarity	NPD5328	Approved
0.6727	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6882	Approved
0.6723	Remote Similarity	NPD6053	Discontinued
0.6723	Remote Similarity	NPD8297	Approved
0.672	Remote Similarity	NPD8328	Phase 3
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD5173	Approved
0.6606	Remote Similarity	NPD6050	Approved
0.6606	Remote Similarity	NPD5693	Phase 1
0.6606	Remote Similarity	NPD5694	Approved
0.6604	Remote Similarity	NPD3618	Phase 1
0.6587	Remote Similarity	NPD7604	Phase 2
0.6581	Remote Similarity	NPD5701	Approved
0.6579	Remote Similarity	NPD5344	Discontinued
0.6562	Remote Similarity	NPD8074	Phase 3
0.656	Remote Similarity	NPD6015	Approved
0.656	Remote Similarity	NPD5983	Phase 2
0.656	Remote Similarity	NPD6016	Approved
0.6557	Remote Similarity	NPD6868	Approved
0.6555	Remote Similarity	NPD6371	Approved
0.6555	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD5211	Phase 2
0.6518	Remote Similarity	NPD7839	Suspended
0.6514	Remote Similarity	NPD6698	Approved
0.6514	Remote Similarity	NPD46	Approved
0.6514	Remote Similarity	NPD7838	Discovery
0.6514	Remote Similarity	NPD5692	Phase 3
0.6509	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5988	Approved
0.6504	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5285	Approved
0.6491	Remote Similarity	NPD4696	Approved
0.6491	Remote Similarity	NPD5286	Approved
0.6484	Remote Similarity	NPD6336	Discontinued
0.648	Remote Similarity	NPD6059	Approved
0.6455	Remote Similarity	NPD8035	Phase 2
0.6455	Remote Similarity	NPD5281	Approved
0.6455	Remote Similarity	NPD5284	Approved
0.6455	Remote Similarity	NPD8034	Phase 2
0.6452	Remote Similarity	NPD6335	Approved
0.6449	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5786	Approved
0.6441	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6845	Suspended
0.6435	Remote Similarity	NPD5223	Approved
0.6434	Remote Similarity	NPD8293	Discontinued
0.6429	Remote Similarity	NPD7503	Approved
0.6422	Remote Similarity	NPD6673	Approved
0.6422	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6051	Approved
0.6422	Remote Similarity	NPD6904	Approved
0.6422	Remote Similarity	NPD6080	Approved
0.641	Remote Similarity	NPD5141	Approved
0.64	Remote Similarity	NPD7100	Approved
0.64	Remote Similarity	NPD7101	Approved
0.6379	Remote Similarity	NPD4633	Approved
0.6379	Remote Similarity	NPD5225	Approved
0.6379	Remote Similarity	NPD5224	Approved
0.6379	Remote Similarity	NPD5226	Approved
0.6371	Remote Similarity	NPD6317	Approved
0.6355	Remote Similarity	NPD5363	Approved
0.6339	Remote Similarity	NPD5282	Discontinued
0.6339	Remote Similarity	NPD6001	Approved
0.6333	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5175	Approved
0.6325	Remote Similarity	NPD5174	Approved
0.632	Remote Similarity	NPD6314	Approved
0.632	Remote Similarity	NPD6313	Approved
0.6316	Remote Similarity	NPD6084	Phase 2
0.6316	Remote Similarity	NPD4755	Approved
0.6316	Remote Similarity	NPD6083	Phase 2
0.6299	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6921	Approved
0.629	Remote Similarity	NPD6274	Approved
0.6283	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD1695	Approved
0.6262	Remote Similarity	NPD3668	Phase 3
0.6262	Remote Similarity	NPD4786	Approved
0.6261	Remote Similarity	NPD5696	Approved
0.6228	Remote Similarity	NPD7732	Phase 3
0.6226	Remote Similarity	NPD3667	Approved
0.6207	Remote Similarity	NPD4700	Approved
0.619	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4695	Discontinued
0.6182	Remote Similarity	NPD5208	Approved
0.6167	Remote Similarity	NPD6412	Phase 2
0.6147	Remote Similarity	NPD6098	Approved
0.6147	Remote Similarity	NPD5279	Phase 3
0.6146	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5654	Approved
0.6136	Remote Similarity	NPD6033	Approved
0.6131	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5168	Approved
0.6116	Remote Similarity	NPD4729	Approved
0.6116	Remote Similarity	NPD4730	Approved
0.6111	Remote Similarity	NPD3666	Approved
0.6111	Remote Similarity	NPD3665	Phase 1
0.6111	Remote Similarity	NPD3133	Approved
0.6107	Remote Similarity	NPD8451	Approved
0.6106	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD6334	Approved
0.6087	Remote Similarity	NPD6333	Approved
0.6078	Remote Similarity	NPD4058	Approved
0.6077	Remote Similarity	NPD7830	Approved
0.6077	Remote Similarity	NPD7829	Approved
0.6075	Remote Similarity	NPD4269	Approved
0.6075	Remote Similarity	NPD4270	Approved
0.6068	Remote Similarity	NPD6404	Discontinued
0.6063	Remote Similarity	NPD7328	Approved
0.6063	Remote Similarity	NPD7327	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