NPASS Compound

Structure

CID72638 OpenBabel06191715412D 33 37 0 0 1 0 0 0 0 0999 V2000 -7.1870 1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7216 2.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 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 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 21 2 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 6 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	5.855
LogD:	4.593
LogS:	-4.707
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.841
Fsp3:	0.9
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:	-5.331
MDCK Permeability:	1.1071698281739373e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.616
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.171
Plasma Protein Binding (PPB):	96.1539077758789%
Volume Distribution (VD):	0.827
Pgp-substrate:	3.153292417526245%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.383
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	2.899
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.113
Carcinogencity:	0.079
Eye Corrosion:	0.489
Eye Irritation:	0.413
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC72638

Natural Product ID:	NPC72638
*Common Name:**	Aleuritolic Acid
IUPAC Name:	(4aS,6aR,6bR,8aR,10S,12aR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6a,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	Aleuritolic Acid; Maprounic Acid
Standard InCHIKey:	BHHPRAFMEFGOLZ-QVUWEPBXSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-25(2)16-17-30(24(32)33)15-10-21-28(6)12-8-19-26(3,4)23(31)11-14-27(19,5)20(28)9-13-29(21,7)22(30)18-25/h10,19-20,22-23,31H,8-9,11-18H2,1-7H3,(H,32,33)/t19-,20+,22-,23-,27-,28+,29+,30+/m0/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@@]2(C1=CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258249
PubChem CID:	161527
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075783]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	leaves and stem	Nakorn Si Thammarat Province, Thailand	2004-MAR	PMID[18179177]
NPO41069	Sapium discolor	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30350995]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631436]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7561895]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27192	Maprounea africana	Species	Euphorbiaceae	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	4
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	24900.0	nM	PMID[523156]
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	50000.0	nM	PMID[523159]
NPT2	Others	Unspecified		IC50	=	78700.0	nM	PMID[523156]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	113.3	%	PMID[523158]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	102.6	%	PMID[523158]
NPT22879	SINGLE PROTEIN	DNA ligase 1	Homo sapiens	IC50	=	95.0	ug.mL-1	PMID[523160]

☑ 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 NPC72638 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	207
0.1-0.2	1387
0.2-0.3	5429
0.3-0.4	15565
0.4-0.5	7870
0.5-0.6	5083
0.6-0.7	4747
0.7-0.8	1863
0.8-0.85	183
0.85-0.9	144
0.9-0.95	149
0.95-1	70

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC293564
0.9877	High Similarity	NPC98442
0.9877	High Similarity	NPC171203
0.9877	High Similarity	NPC307426
0.9877	High Similarity	NPC88716
0.9877	High Similarity	NPC142415
0.9877	High Similarity	NPC102683
0.9877	High Similarity	NPC68160
0.9877	High Similarity	NPC130577
0.9877	High Similarity	NPC18064
0.9877	High Similarity	NPC51700
0.9877	High Similarity	NPC242468
0.9756	High Similarity	NPC181225
0.9756	High Similarity	NPC474512
0.9756	High Similarity	NPC52169
0.9756	High Similarity	NPC470629
0.9756	High Similarity	NPC246708
0.9756	High Similarity	NPC290690
0.9756	High Similarity	NPC182797
0.9756	High Similarity	NPC40552
0.9756	High Similarity	NPC473242
0.9756	High Similarity	NPC17733
0.9639	High Similarity	NPC127689
0.9639	High Similarity	NPC474972
0.9639	High Similarity	NPC293048
0.9639	High Similarity	NPC61543
0.9639	High Similarity	NPC25906
0.9639	High Similarity	NPC198664
0.9639	High Similarity	NPC225585
0.9639	High Similarity	NPC95246
0.9639	High Similarity	NPC130520
0.9639	High Similarity	NPC143232
0.9639	High Similarity	NPC59263
0.9639	High Similarity	NPC290972
0.9639	High Similarity	NPC121798
0.9639	High Similarity	NPC263393
0.9639	High Similarity	NPC234346
0.9639	High Similarity	NPC64872
0.9639	High Similarity	NPC161751
0.9639	High Similarity	NPC274330
0.9639	High Similarity	NPC470588
0.9639	High Similarity	NPC270768
0.9524	High Similarity	NPC477872
0.9524	High Similarity	NPC470589
0.9524	High Similarity	NPC86372
0.9524	High Similarity	NPC7260
0.9524	High Similarity	NPC120968
0.9524	High Similarity	NPC273621
0.9524	High Similarity	NPC227467
0.9524	High Similarity	NPC126369
0.9524	High Similarity	NPC130278
0.9524	High Similarity	NPC111110
0.9524	High Similarity	NPC18872
0.9524	High Similarity	NPC49320
0.9524	High Similarity	NPC290614
0.9524	High Similarity	NPC291028
0.9524	High Similarity	NPC172361
0.9524	High Similarity	NPC210037
0.9506	High Similarity	NPC171789
0.9412	High Similarity	NPC65120
0.9412	High Similarity	NPC282616
0.9412	High Similarity	NPC474525
0.9412	High Similarity	NPC966
0.9412	High Similarity	NPC235884
0.9412	High Similarity	NPC187722
0.9412	High Similarity	NPC475708
0.9412	High Similarity	NPC155120
0.9412	High Similarity	NPC52021
0.9412	High Similarity	NPC228784
0.9412	High Similarity	NPC71074
0.9412	High Similarity	NPC300351
0.9412	High Similarity	NPC158030
0.9412	High Similarity	NPC306541
0.9412	High Similarity	NPC84319
0.9412	High Similarity	NPC233455
0.9412	High Similarity	NPC25299
0.9412	High Similarity	NPC288833
0.9412	High Similarity	NPC4036
0.9412	High Similarity	NPC145067
0.9412	High Similarity	NPC105189
0.9412	High Similarity	NPC472149
0.9412	High Similarity	NPC324341
0.9405	High Similarity	NPC474686
0.9405	High Similarity	NPC30522
0.9398	High Similarity	NPC71507
0.939	High Similarity	NPC133954
0.9302	High Similarity	NPC202728
0.9302	High Similarity	NPC295643
0.9302	High Similarity	NPC272075
0.9302	High Similarity	NPC229281
0.9302	High Similarity	NPC298554
0.9302	High Similarity	NPC49776
0.9302	High Similarity	NPC474436
0.9302	High Similarity	NPC214756
0.9302	High Similarity	NPC136313
0.9302	High Similarity	NPC86368
0.9302	High Similarity	NPC275809
0.9302	High Similarity	NPC74855
0.9302	High Similarity	NPC307335
0.9302	High Similarity	NPC63118
0.9302	High Similarity	NPC158059
0.9302	High Similarity	NPC118519
0.9294	High Similarity	NPC46441
0.9294	High Similarity	NPC474728
0.9294	High Similarity	NPC193750
0.9294	High Similarity	NPC113989
0.9294	High Similarity	NPC120840
0.9277	High Similarity	NPC235341
0.9277	High Similarity	NPC74363
0.9277	High Similarity	NPC475862
0.9277	High Similarity	NPC213412
0.9277	High Similarity	NPC95594
0.9277	High Similarity	NPC477579
0.9195	High Similarity	NPC91010
0.9195	High Similarity	NPC32407
0.9195	High Similarity	NPC231063
0.9195	High Similarity	NPC209868
0.9195	High Similarity	NPC263548
0.9195	High Similarity	NPC299996
0.9195	High Similarity	NPC145667
0.9195	High Similarity	NPC159365
0.9195	High Similarity	NPC20235
0.9195	High Similarity	NPC282395
0.9195	High Similarity	NPC114159
0.9195	High Similarity	NPC6818
0.9195	High Similarity	NPC222047
0.9195	High Similarity	NPC88116
0.9195	High Similarity	NPC474529
0.9195	High Similarity	NPC191412
0.9186	High Similarity	NPC6255
0.9186	High Similarity	NPC301244
0.9186	High Similarity	NPC38754
0.9186	High Similarity	NPC77099
0.9186	High Similarity	NPC60755
0.9186	High Similarity	NPC285184
0.9186	High Similarity	NPC471588
0.9186	High Similarity	NPC470590
0.9167	High Similarity	NPC73064
0.9091	High Similarity	NPC474727
0.9091	High Similarity	NPC96916
0.9091	High Similarity	NPC198245
0.9091	High Similarity	NPC139570
0.9091	High Similarity	NPC148523
0.9091	High Similarity	NPC473240
0.908	High Similarity	NPC118490
0.908	High Similarity	NPC474806
0.908	High Similarity	NPC133579
0.9048	High Similarity	NPC325594
0.9048	High Similarity	NPC10005
0.9048	High Similarity	NPC9892
0.9048	High Similarity	NPC56588
0.9048	High Similarity	NPC73038
0.9048	High Similarity	NPC91525
0.9048	High Similarity	NPC329943
0.9036	High Similarity	NPC180834
0.8989	High Similarity	NPC157113
0.8989	High Similarity	NPC204961
0.8989	High Similarity	NPC98874
0.8989	High Similarity	NPC207922
0.8989	High Similarity	NPC476318
0.8989	High Similarity	NPC132824
0.8989	High Similarity	NPC158371
0.8989	High Similarity	NPC327179
0.8989	High Similarity	NPC173744
0.8989	High Similarity	NPC62516
0.8989	High Similarity	NPC201657
0.8989	High Similarity	NPC259733
0.8989	High Similarity	NPC116457
0.8989	High Similarity	NPC476327
0.8989	High Similarity	NPC307282
0.8989	High Similarity	NPC19376
0.8989	High Similarity	NPC230151
0.8989	High Similarity	NPC305464
0.8989	High Similarity	NPC73004
0.8989	High Similarity	NPC25848
0.8977	High Similarity	NPC87095
0.8977	High Similarity	NPC184006
0.8977	High Similarity	NPC188102
0.8977	High Similarity	NPC23621
0.8977	High Similarity	NPC60692
0.8977	High Similarity	NPC80365
0.8977	High Similarity	NPC296164
0.8977	High Similarity	NPC78580
0.8977	High Similarity	NPC74751
0.8953	High Similarity	NPC281524
0.8953	High Similarity	NPC69627
0.8941	High Similarity	NPC173089
0.8941	High Similarity	NPC158141
0.8941	High Similarity	NPC474684
0.8941	High Similarity	NPC162107
0.8941	High Similarity	NPC46912
0.8941	High Similarity	NPC142361
0.8929	High Similarity	NPC191965
0.8902	High Similarity	NPC274050
0.8902	High Similarity	NPC263272
0.8902	High Similarity	NPC3915
0.8902	High Similarity	NPC162632
0.8902	High Similarity	NPC473420
0.8902	High Similarity	NPC267691
0.8889	High Similarity	NPC476878

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 NPC72638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1817
0.2-0.3	3945
0.3-0.4	2154
0.4-0.5	613
0.5-0.6	190
0.6-0.7	190
0.7-0.8	49
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD7515	Phase 2
0.8977	High Similarity	NPD7748	Approved
0.8706	High Similarity	NPD7520	Clinical (unspecified phase)
0.8681	High Similarity	NPD7902	Approved
0.8434	Intermediate Similarity	NPD7645	Phase 2
0.8352	Intermediate Similarity	NPD7900	Approved
0.8352	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3618	Phase 1
0.8161	Intermediate Similarity	NPD4786	Approved
0.814	Intermediate Similarity	NPD3667	Approved
0.8111	Intermediate Similarity	NPD5328	Approved
0.7935	Intermediate Similarity	NPD6079	Approved
0.7935	Intermediate Similarity	NPD8035	Phase 2
0.7935	Intermediate Similarity	NPD8034	Phase 2
0.7912	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6399	Phase 3
0.7802	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD3666	Approved
0.7753	Intermediate Similarity	NPD3133	Approved
0.7753	Intermediate Similarity	NPD3665	Phase 1
0.766	Intermediate Similarity	NPD4202	Approved
0.7647	Intermediate Similarity	NPD6117	Approved
0.7629	Intermediate Similarity	NPD7638	Approved
0.7619	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD6409	Approved
0.7582	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD7334	Approved
0.7582	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD6684	Approved
0.7558	Intermediate Similarity	NPD6116	Phase 1
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7525	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD6402	Approved
0.7525	Intermediate Similarity	NPD5739	Approved
0.7525	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7471	Intermediate Similarity	NPD6697	Approved
0.7471	Intermediate Similarity	NPD6115	Approved
0.7471	Intermediate Similarity	NPD6118	Approved
0.7471	Intermediate Similarity	NPD6114	Approved
0.7423	Intermediate Similarity	NPD4697	Phase 3
0.7423	Intermediate Similarity	NPD5222	Approved
0.7423	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7614	Phase 1
0.7423	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD6903	Approved
0.7379	Intermediate Similarity	NPD6881	Approved
0.7379	Intermediate Similarity	NPD6899	Approved
0.7379	Intermediate Similarity	NPD7320	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7363	Intermediate Similarity	NPD3668	Phase 3
0.7347	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD5173	Approved
0.7347	Intermediate Similarity	NPD4755	Approved
0.7347	Intermediate Similarity	NPD6084	Phase 2
0.7326	Intermediate Similarity	NPD6942	Approved
0.7326	Intermediate Similarity	NPD7339	Approved
0.7308	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6373	Approved
0.7308	Intermediate Similarity	NPD6372	Approved
0.7282	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD5701	Approved
0.7241	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7102	Approved
0.7238	Intermediate Similarity	NPD6883	Approved
0.7238	Intermediate Similarity	NPD7290	Approved
0.7234	Intermediate Similarity	NPD5737	Approved
0.7234	Intermediate Similarity	NPD6672	Approved
0.7212	Intermediate Similarity	NPD6011	Approved
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5286	Approved
0.72	Intermediate Similarity	NPD4700	Approved
0.72	Intermediate Similarity	NPD5285	Approved
0.72	Intermediate Similarity	NPD4696	Approved
0.7176	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6869	Approved
0.717	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8130	Phase 1
0.717	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6847	Approved
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4753	Phase 2
0.7158	Intermediate Similarity	NPD6101	Approved
0.7156	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6013	Approved
0.7129	Intermediate Similarity	NPD5223	Approved
0.7111	Intermediate Similarity	NPD4695	Discontinued
0.7103	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD5329	Approved
0.708	Intermediate Similarity	NPD8328	Phase 3
0.7079	Intermediate Similarity	NPD3617	Approved
0.7071	Intermediate Similarity	NPD7732	Phase 3
0.7065	Intermediate Similarity	NPD4788	Approved
0.7059	Intermediate Similarity	NPD5225	Approved
0.7059	Intermediate Similarity	NPD5226	Approved
0.7059	Intermediate Similarity	NPD5224	Approved
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7059	Intermediate Similarity	NPD4633	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7021	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.699	Remote Similarity	NPD5175	Approved
0.699	Remote Similarity	NPD5174	Approved
0.699	Remote Similarity	NPD4754	Approved
0.6989	Remote Similarity	NPD4197	Approved
0.697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5695	Phase 3
0.6932	Remote Similarity	NPD3703	Phase 2
0.6931	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD5141	Approved
0.6915	Remote Similarity	NPD1694	Approved
0.6909	Remote Similarity	NPD6868	Approved
0.6881	Remote Similarity	NPD4632	Approved
0.686	Remote Similarity	NPD4244	Approved
0.686	Remote Similarity	NPD4245	Approved
0.6857	Remote Similarity	NPD4768	Approved
0.6857	Remote Similarity	NPD4767	Approved
0.6842	Remote Similarity	NPD5205	Approved
0.6842	Remote Similarity	NPD4138	Approved
0.6842	Remote Similarity	NPD4689	Approved
0.6842	Remote Similarity	NPD4688	Approved
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD4690	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6842	Remote Similarity	NPD4693	Phase 3
0.6837	Remote Similarity	NPD5281	Approved
0.6837	Remote Similarity	NPD5284	Approved
0.6822	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6904	Approved
0.6804	Remote Similarity	NPD6080	Approved
0.6804	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD5210	Approved
0.68	Remote Similarity	NPD4629	Approved
0.6792	Remote Similarity	NPD6412	Phase 2
0.6786	Remote Similarity	NPD6335	Approved
0.6786	Remote Similarity	NPD4224	Phase 2
0.6774	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5778	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD6274	Approved
0.6744	Remote Similarity	NPD3698	Phase 2
0.6729	Remote Similarity	NPD4730	Approved
0.6729	Remote Similarity	NPD5168	Approved
0.6729	Remote Similarity	NPD4729	Approved
0.6729	Remote Similarity	NPD5128	Approved
0.6726	Remote Similarity	NPD7100	Approved
0.6726	Remote Similarity	NPD7101	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5208	Approved
0.67	Remote Similarity	NPD6001	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6637	Remote Similarity	NPD6314	Approved
0.6637	Remote Similarity	NPD6313	Approved
0.6629	Remote Similarity	NPD6924	Approved
0.6629	Remote Similarity	NPD6926	Approved
0.6628	Remote Similarity	NPD5360	Phase 3
0.6628	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6908	Approved
0.6609	Remote Similarity	NPD6909	Approved
0.6606	Remote Similarity	NPD5251	Approved
0.6606	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5250	Approved
0.6606	Remote Similarity	NPD5249	Phase 3
0.6606	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5247	Approved
0.6606	Remote Similarity	NPD5248	Approved
0.6606	Remote Similarity	NPD5169	Approved
0.6606	Remote Similarity	NPD5135	Approved
0.6606	Remote Similarity	NPD4634	Approved
0.6591	Remote Similarity	NPD4243	Approved
0.6591	Remote Similarity	NPD6081	Approved
0.6591	Remote Similarity	NPD5777	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6686	Approved
0.6559	Remote Similarity	NPD4748	Discontinued
0.6559	Remote Similarity	NPD8259	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