NPASS Compound

Structure

NPC140723 OpenBabel07101718302D 34 38 0 0 1 0 0 0 0 0999 V2000 3.2372 -4.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5244 -3.1396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 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 -0.4067 1.9135 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 1.8990 -2.8122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8771 -2.6043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2298 -2.0691 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 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 3.5462 -3.3475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.1180 0.0000 C 0 0 2 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 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -0.8090 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 -2.5981 1.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 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 3.2989 -1.3968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 17 2 0 0 0 0 11 12 1 0 0 0 0 11 19 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 24 1 0 0 0 0 16 29 1 0 0 0 0 18 10 1 6 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 28 1 6 0 0 0 21 16 1 6 0 0 0 21 25 1 0 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 30 1 6 0 0 0 24 32 1 0 0 0 0 25 30 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	509.269
LogP:	5.89
LogD:	4.229
LogS:	-5.859
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.213
Fsp3:	0.8
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:	-4.941
MDCK Permeability:	3.0003366191522218e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.763

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.542
Plasma Protein Binding (PPB):	94.1295394897461%
Volume Distribution (VD):	1.568
Pgp-substrate:	4.153745651245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.333
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.396
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	7.661
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.549
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.1
Carcinogencity:	0.071
Eye Corrosion:	0.014
Eye Irritation:	0.114
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC140723

Natural Product ID:	NPC140723
*Common Name:**	UBPWASPNRWXDEI-UHJNRKMWSA-N
IUPAC Name:	n.a.
Synonyms:	12Beta-Hydroxykulactone
Standard InCHIKey:	UBPWASPNRWXDEI-UHJNRKMWSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-17(2)9-8-10-18-25-21(34-26(18)33)16-29(6)19-11-12-22-27(3,4)23(31)13-14-28(22,5)20(19)15-24(32)30(25,29)7/h9,11,18,20-22,24-25,32H,8,10,12-16H2,1-7H3/t18-,20+,21+,22+,24-,25-,28-,29-,30+/m1/s1
SMILES:	CC(=CCC[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@H]5C(C)(C)C(=O)CC[C@]5(C)[C@H]4C[C@H]([C@@]23C)O)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464813
PubChem CID:	10367373
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217705]
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461654]
NPO4571	Melia volkensii	Species	Meliaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	16.0	ug.mL-1	PMID[507835]

☑ 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 NPC140723 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	205
0.1-0.2	1269
0.2-0.3	5037
0.3-0.4	11365
0.4-0.5	9911
0.5-0.6	5564
0.6-0.7	6193
0.7-0.8	2836
0.8-0.85	265
0.85-0.9	45
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC218383
0.92	High Similarity	NPC278628
0.92	High Similarity	NPC231530
0.9175	High Similarity	NPC271387
0.9175	High Similarity	NPC153792
0.9135	High Similarity	NPC52634
0.91	High Similarity	NPC29705
0.902	High Similarity	NPC94529
0.901	High Similarity	NPC196528
0.8962	High Similarity	NPC266728
0.8962	High Similarity	NPC49492
0.8947	High Similarity	NPC154101
0.8922	High Similarity	NPC59530
0.8911	High Similarity	NPC471293
0.89	High Similarity	NPC22388
0.8878	High Similarity	NPC475894
0.8866	High Similarity	NPC469599
0.8854	High Similarity	NPC470224
0.8854	High Similarity	NPC470375
0.8854	High Similarity	NPC470376
0.8846	High Similarity	NPC197428
0.8824	High Similarity	NPC96377
0.88	High Similarity	NPC474327
0.8788	High Similarity	NPC477854
0.8776	High Similarity	NPC173272
0.8776	High Similarity	NPC42042
0.8774	High Similarity	NPC202889
0.8774	High Similarity	NPC962
0.8738	High Similarity	NPC220974
0.8725	High Similarity	NPC96268
0.8725	High Similarity	NPC472227
0.8725	High Similarity	NPC472228
0.8725	High Similarity	NPC255309
0.8692	High Similarity	NPC471398
0.8687	High Similarity	NPC190554
0.8679	High Similarity	NPC71348
0.8679	High Similarity	NPC280782
0.8673	High Similarity	NPC69548
0.8673	High Similarity	NPC48330
0.8673	High Similarity	NPC184848
0.866	High Similarity	NPC206810
0.8636	High Similarity	NPC109973
0.8632	High Similarity	NPC28227
0.8627	High Similarity	NPC159442
0.8627	High Similarity	NPC36688
0.8614	High Similarity	NPC121218
0.8614	High Similarity	NPC253886
0.8614	High Similarity	NPC39683
0.8611	High Similarity	NPC270958
0.86	High Similarity	NPC477813
0.8598	High Similarity	NPC250109
0.8586	High Similarity	NPC200054
0.8586	High Similarity	NPC477853
0.8586	High Similarity	NPC29410
0.8586	High Similarity	NPC49371
0.8585	High Similarity	NPC118860
0.8585	High Similarity	NPC214797
0.8585	High Similarity	NPC231589
0.8571	High Similarity	NPC241927
0.8571	High Similarity	NPC258543
0.8571	High Similarity	NPC111015
0.8557	High Similarity	NPC150383
0.8557	High Similarity	NPC23434
0.8544	High Similarity	NPC477812
0.8544	High Similarity	NPC164835
0.8544	High Similarity	NPC228669
0.8542	High Similarity	NPC54689
0.8529	High Similarity	NPC473928
0.8529	High Similarity	NPC136289
0.8529	High Similarity	NPC170615
0.8526	High Similarity	NPC167877
0.8519	High Similarity	NPC326542
0.8515	High Similarity	NPC83709
0.8515	High Similarity	NPC108371
0.8515	High Similarity	NPC15390
0.8515	High Similarity	NPC267921
0.8515	High Similarity	NPC167974
0.8505	High Similarity	NPC170487
0.8505	High Similarity	NPC207251
0.85	High Similarity	NPC107243
0.85	High Similarity	NPC57416
0.8485	Intermediate Similarity	NPC45324
0.8485	Intermediate Similarity	NPC98639
0.8485	Intermediate Similarity	NPC279974
0.8485	Intermediate Similarity	NPC162001
0.8485	Intermediate Similarity	NPC222845
0.8482	Intermediate Similarity	NPC222688
0.8476	Intermediate Similarity	NPC258323
0.8476	Intermediate Similarity	NPC469845
0.8469	Intermediate Similarity	NPC107674
0.8469	Intermediate Similarity	NPC66429
0.8469	Intermediate Similarity	NPC170220
0.8469	Intermediate Similarity	NPC152897
0.8469	Intermediate Similarity	NPC141497
0.8469	Intermediate Similarity	NPC477855
0.8462	Intermediate Similarity	NPC470309
0.8462	Intermediate Similarity	NPC102352
0.8462	Intermediate Similarity	NPC475571
0.8455	Intermediate Similarity	NPC118638
0.8454	Intermediate Similarity	NPC471896
0.8447	Intermediate Similarity	NPC474775
0.8447	Intermediate Similarity	NPC236390
0.8447	Intermediate Similarity	NPC36321
0.8438	Intermediate Similarity	NPC294480
0.8431	Intermediate Similarity	NPC81530
0.8416	Intermediate Similarity	NPC471038
0.8416	Intermediate Similarity	NPC38471
0.8416	Intermediate Similarity	NPC20479
0.8416	Intermediate Similarity	NPC119036
0.8416	Intermediate Similarity	NPC98837
0.8416	Intermediate Similarity	NPC38296
0.8416	Intermediate Similarity	NPC162459
0.8416	Intermediate Similarity	NPC28864
0.8416	Intermediate Similarity	NPC114274
0.8416	Intermediate Similarity	NPC176845
0.84	Intermediate Similarity	NPC304899
0.84	Intermediate Similarity	NPC253115
0.84	Intermediate Similarity	NPC322063
0.8396	Intermediate Similarity	NPC304495
0.8384	Intermediate Similarity	NPC159410
0.8381	Intermediate Similarity	NPC230541
0.8381	Intermediate Similarity	NPC144854
0.8381	Intermediate Similarity	NPC44063
0.8381	Intermediate Similarity	NPC3316
0.8378	Intermediate Similarity	NPC475041
0.8367	Intermediate Similarity	NPC110657
0.8367	Intermediate Similarity	NPC297265
0.8367	Intermediate Similarity	NPC86266
0.8367	Intermediate Similarity	NPC212301
0.8365	Intermediate Similarity	NPC47281
0.8365	Intermediate Similarity	NPC235889
0.8365	Intermediate Similarity	NPC28656
0.8351	Intermediate Similarity	NPC475921
0.8351	Intermediate Similarity	NPC474704
0.8351	Intermediate Similarity	NPC477943
0.8351	Intermediate Similarity	NPC474679
0.835	Intermediate Similarity	NPC271980
0.835	Intermediate Similarity	NPC195290
0.835	Intermediate Similarity	NPC193934
0.835	Intermediate Similarity	NPC204450
0.8349	Intermediate Similarity	NPC123117
0.8333	Intermediate Similarity	NPC312215
0.8333	Intermediate Similarity	NPC293866
0.8333	Intermediate Similarity	NPC154072
0.8333	Intermediate Similarity	NPC474684
0.8333	Intermediate Similarity	NPC126691
0.8333	Intermediate Similarity	NPC476274
0.8333	Intermediate Similarity	NPC142361
0.8318	Intermediate Similarity	NPC101450
0.8318	Intermediate Similarity	NPC163314
0.8318	Intermediate Similarity	NPC42776
0.8318	Intermediate Similarity	NPC76084
0.8317	Intermediate Similarity	NPC253586
0.8317	Intermediate Similarity	NPC475032
0.8317	Intermediate Similarity	NPC108078
0.8317	Intermediate Similarity	NPC475033
0.8316	Intermediate Similarity	NPC474218
0.8316	Intermediate Similarity	NPC470223
0.8302	Intermediate Similarity	NPC275539
0.8302	Intermediate Similarity	NPC189075
0.8302	Intermediate Similarity	NPC154608
0.8302	Intermediate Similarity	NPC192813
0.8302	Intermediate Similarity	NPC469844
0.8302	Intermediate Similarity	NPC277017
0.8302	Intermediate Similarity	NPC19412
0.83	Intermediate Similarity	NPC263347
0.83	Intermediate Similarity	NPC470016
0.83	Intermediate Similarity	NPC317586
0.83	Intermediate Similarity	NPC472485
0.8286	Intermediate Similarity	NPC50692
0.8286	Intermediate Similarity	NPC49958
0.8286	Intermediate Similarity	NPC260268
0.8286	Intermediate Similarity	NPC28791
0.8286	Intermediate Similarity	NPC37600
0.8286	Intermediate Similarity	NPC150531
0.8286	Intermediate Similarity	NPC476027
0.8286	Intermediate Similarity	NPC302607
0.8286	Intermediate Similarity	NPC296945
0.8286	Intermediate Similarity	NPC295366
0.8286	Intermediate Similarity	NPC152695
0.8286	Intermediate Similarity	NPC48733
0.8286	Intermediate Similarity	NPC97202
0.8286	Intermediate Similarity	NPC202167
0.8286	Intermediate Similarity	NPC85829
0.8286	Intermediate Similarity	NPC50535
0.8286	Intermediate Similarity	NPC171137
0.8286	Intermediate Similarity	NPC214264
0.8286	Intermediate Similarity	NPC319077
0.8286	Intermediate Similarity	NPC181265
0.8283	Intermediate Similarity	NPC224060
0.8283	Intermediate Similarity	NPC244356
0.8283	Intermediate Similarity	NPC243866
0.8273	Intermediate Similarity	NPC196931
0.8269	Intermediate Similarity	NPC55872
0.8269	Intermediate Similarity	NPC221421
0.8269	Intermediate Similarity	NPC191892
0.8269	Intermediate Similarity	NPC87927
0.8269	Intermediate Similarity	NPC95585
0.8269	Intermediate Similarity	NPC469985
0.8269	Intermediate Similarity	NPC117185

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 NPC140723 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1546
0.2-0.3	4082
0.3-0.4	2251
0.4-0.5	597
0.5-0.6	165
0.6-0.7	170
0.7-0.8	123
0.8-0.85	42
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD6008	Approved
0.8654	High Similarity	NPD7320	Approved
0.8641	High Similarity	NPD7128	Approved
0.8641	High Similarity	NPD6675	Approved
0.8641	High Similarity	NPD6402	Approved
0.8641	High Similarity	NPD5739	Approved
0.8571	High Similarity	NPD6373	Approved
0.8571	High Similarity	NPD6372	Approved
0.8476	Intermediate Similarity	NPD6881	Approved
0.8476	Intermediate Similarity	NPD6899	Approved
0.8469	Intermediate Similarity	NPD6399	Phase 3
0.8411	Intermediate Similarity	NPD6650	Approved
0.8411	Intermediate Similarity	NPD6649	Approved
0.8381	Intermediate Similarity	NPD5701	Approved
0.8381	Intermediate Similarity	NPD5697	Approved
0.8318	Intermediate Similarity	NPD7102	Approved
0.8318	Intermediate Similarity	NPD7290	Approved
0.8318	Intermediate Similarity	NPD6883	Approved
0.8302	Intermediate Similarity	NPD6011	Approved
0.83	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8257	Intermediate Similarity	NPD4632	Approved
0.8241	Intermediate Similarity	NPD6869	Approved
0.8241	Intermediate Similarity	NPD6617	Approved
0.8241	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD8130	Phase 1
0.8241	Intermediate Similarity	NPD6847	Approved
0.8224	Intermediate Similarity	NPD6012	Approved
0.8224	Intermediate Similarity	NPD6014	Approved
0.8224	Intermediate Similarity	NPD6013	Approved
0.8174	Intermediate Similarity	NPD7492	Approved
0.8165	Intermediate Similarity	NPD8297	Approved
0.8165	Intermediate Similarity	NPD6882	Approved
0.8163	Intermediate Similarity	NPD5328	Approved
0.8142	Intermediate Similarity	NPD6059	Approved
0.8142	Intermediate Similarity	NPD6054	Approved
0.8137	Intermediate Similarity	NPD6083	Phase 2
0.8137	Intermediate Similarity	NPD4755	Approved
0.8137	Intermediate Similarity	NPD6084	Phase 2
0.8103	Intermediate Similarity	NPD6616	Approved
0.8061	Intermediate Similarity	NPD6903	Approved
0.8058	Intermediate Similarity	NPD7638	Approved
0.8041	Intermediate Similarity	NPD7146	Approved
0.8041	Intermediate Similarity	NPD5330	Approved
0.8041	Intermediate Similarity	NPD7334	Approved
0.8041	Intermediate Similarity	NPD6684	Approved
0.8041	Intermediate Similarity	NPD7521	Approved
0.8041	Intermediate Similarity	NPD6409	Approved
0.8036	Intermediate Similarity	NPD6009	Approved
0.8034	Intermediate Similarity	NPD7078	Approved
0.8034	Intermediate Similarity	NPD8293	Discontinued
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD6370	Approved
0.7982	Intermediate Similarity	NPD6319	Approved
0.7981	Intermediate Similarity	NPD5286	Approved
0.7981	Intermediate Similarity	NPD7640	Approved
0.7981	Intermediate Similarity	NPD7639	Approved
0.7981	Intermediate Similarity	NPD5285	Approved
0.7981	Intermediate Similarity	NPD4700	Approved
0.7981	Intermediate Similarity	NPD4696	Approved
0.7966	Intermediate Similarity	NPD7736	Approved
0.7931	Intermediate Similarity	NPD7604	Phase 2
0.7921	Intermediate Similarity	NPD4202	Approved
0.7913	Intermediate Similarity	NPD6016	Approved
0.7913	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD5983	Phase 2
0.7913	Intermediate Similarity	NPD6015	Approved
0.7905	Intermediate Similarity	NPD5223	Approved
0.7885	Intermediate Similarity	NPD5696	Approved
0.7879	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6412	Phase 2
0.7864	Intermediate Similarity	NPD4697	Phase 3
0.7857	Intermediate Similarity	NPD3618	Phase 1
0.7845	Intermediate Similarity	NPD5988	Approved
0.7843	Intermediate Similarity	NPD6001	Approved
0.7835	Intermediate Similarity	NPD3666	Approved
0.7835	Intermediate Similarity	NPD3133	Approved
0.7835	Intermediate Similarity	NPD4786	Approved
0.7835	Intermediate Similarity	NPD3665	Phase 1
0.783	Intermediate Similarity	NPD5225	Approved
0.783	Intermediate Similarity	NPD5226	Approved
0.783	Intermediate Similarity	NPD5224	Approved
0.783	Intermediate Similarity	NPD5211	Phase 2
0.783	Intermediate Similarity	NPD4633	Approved
0.7822	Intermediate Similarity	NPD8034	Phase 2
0.7822	Intermediate Similarity	NPD8035	Phase 2
0.7807	Intermediate Similarity	NPD6335	Approved
0.7797	Intermediate Similarity	NPD6336	Discontinued
0.7788	Intermediate Similarity	NPD7902	Approved
0.7788	Intermediate Similarity	NPD6274	Approved
0.7767	Intermediate Similarity	NPD5695	Phase 3
0.7757	Intermediate Similarity	NPD4754	Approved
0.7757	Intermediate Similarity	NPD5175	Approved
0.7757	Intermediate Similarity	NPD5174	Approved
0.7739	Intermediate Similarity	NPD7101	Approved
0.7739	Intermediate Similarity	NPD7100	Approved
0.7719	Intermediate Similarity	NPD6317	Approved
0.77	Intermediate Similarity	NPD6672	Approved
0.77	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD5221	Approved
0.7692	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5222	Approved
0.7685	Intermediate Similarity	NPD5141	Approved
0.7679	Intermediate Similarity	NPD6053	Discontinued
0.7677	Intermediate Similarity	NPD6098	Approved
0.767	Intermediate Similarity	NPD7748	Approved
0.7667	Intermediate Similarity	NPD6033	Approved
0.7658	Intermediate Similarity	NPD4634	Approved
0.7652	Intermediate Similarity	NPD6314	Approved
0.7652	Intermediate Similarity	NPD6313	Approved
0.7647	Intermediate Similarity	NPD7507	Approved
0.7647	Intermediate Similarity	NPD5284	Approved
0.7647	Intermediate Similarity	NPD5281	Approved
0.7647	Intermediate Similarity	NPD7515	Phase 2
0.7629	Intermediate Similarity	NPD3667	Approved
0.7624	Intermediate Similarity	NPD6904	Approved
0.7624	Intermediate Similarity	NPD6673	Approved
0.7624	Intermediate Similarity	NPD6080	Approved
0.7624	Intermediate Similarity	NPD4753	Phase 2
0.7619	Intermediate Similarity	NPD5173	Approved
0.7615	Intermediate Similarity	NPD4768	Approved
0.7615	Intermediate Similarity	NPD4767	Approved
0.7607	Intermediate Similarity	NPD6909	Approved
0.7607	Intermediate Similarity	NPD6908	Approved
0.7576	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD5207	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7900	Approved
0.7479	Intermediate Similarity	NPD6067	Discontinued
0.7478	Intermediate Similarity	NPD6868	Approved
0.7477	Intermediate Similarity	NPD4729	Approved
0.7477	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD4730	Approved
0.7459	Intermediate Similarity	NPD7319	Approved
0.7449	Intermediate Similarity	NPD4221	Approved
0.7449	Intermediate Similarity	NPD4223	Phase 3
0.7449	Intermediate Similarity	NPD6435	Approved
0.7429	Intermediate Similarity	NPD5210	Approved
0.7429	Intermediate Similarity	NPD4629	Approved
0.74	Intermediate Similarity	NPD5329	Approved
0.7353	Intermediate Similarity	NPD5208	Approved
0.7345	Intermediate Similarity	NPD5135	Approved
0.7345	Intermediate Similarity	NPD5248	Approved
0.7345	Intermediate Similarity	NPD5251	Approved
0.7345	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5250	Approved
0.7345	Intermediate Similarity	NPD5169	Approved
0.7345	Intermediate Similarity	NPD5249	Phase 3
0.7345	Intermediate Similarity	NPD5247	Approved
0.7339	Intermediate Similarity	NPD7632	Discontinued
0.7327	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5693	Phase 1
0.7308	Intermediate Similarity	NPD6050	Approved
0.7308	Intermediate Similarity	NPD6411	Approved
0.73	Intermediate Similarity	NPD4197	Approved
0.7281	Intermediate Similarity	NPD5216	Approved
0.7281	Intermediate Similarity	NPD5215	Approved
0.7281	Intermediate Similarity	NPD5127	Approved
0.7281	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD6052	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7257	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7525	Registered
0.7245	Intermediate Similarity	NPD5368	Approved
0.7216	Intermediate Similarity	NPD6115	Approved
0.7216	Intermediate Similarity	NPD6114	Approved
0.7216	Intermediate Similarity	NPD6697	Approved
0.7216	Intermediate Similarity	NPD6118	Approved
0.7212	Intermediate Similarity	NPD5692	Phase 3
0.72	Intermediate Similarity	NPD4788	Approved
0.719	Intermediate Similarity	NPD8328	Phase 3
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4693	Phase 3
0.7157	Intermediate Similarity	NPD4690	Approved
0.7157	Intermediate Similarity	NPD5205	Approved
0.7157	Intermediate Similarity	NPD4138	Approved
0.7157	Intermediate Similarity	NPD4688	Approved
0.7157	Intermediate Similarity	NPD5279	Phase 3
0.7157	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD5694	Approved
0.7132	Intermediate Similarity	NPD6333	Approved
0.7132	Intermediate Similarity	NPD6334	Approved
0.7129	Intermediate Similarity	NPD3668	Phase 3
0.7115	Intermediate Similarity	NPD6051	Approved
0.7115	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6101	Approved
0.7113	Intermediate Similarity	NPD6116	Phase 1
0.7094	Intermediate Similarity	NPD5167	Approved
0.7087	Intermediate Similarity	NPD3573	Approved
0.7075	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD7327	Approved
0.703	Intermediate Similarity	NPD5362	Discontinued
0.7018	Intermediate Similarity	NPD6686	Approved
0.7018	Intermediate Similarity	NPD5168	Approved
0.701	Intermediate Similarity	NPD6117	Approved
0.701	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD5369	Approved
0.699	Remote Similarity	NPD5280	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