NPASS Compound

Structure

CID271980 OpenBabel06191716082D 35 39 0 0 1 0 0 0 0 0999 V2000 -3.1369 6.4431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5278 5.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4325 3.1338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5409 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -2.4763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5401 -0.5218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7400 4.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7847 4.7884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0415 3.6561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 -0.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6940 1.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2329 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4831 5.7174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3878 2.9305 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3875 1.9538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9777 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6935 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6926 -0.9772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2326 0.4876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8460 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6928 -1.9549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5406 1.4652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8466 -1.4663 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5403 0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8469 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5604 -1.4778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9409 -0.2210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 1.4910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -1.4663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6928 -2.9321 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 4 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 29 1 0 0 0 0 18 3 1 1 0 0 0 18 19 1 0 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 20 30 1 0 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 27 1 6 0 0 0 22 31 1 0 0 0 0 23 28 1 1 0 0 0 23 32 1 0 0 0 0 24 30 1 1 0 0 0 24 33 1 0 0 0 0 25 27 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 28 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	523.332
LogP:	4.273
LogD:	3.896
LogS:	-3.759
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	6.034
Fsp3:	0.9
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:	-5.602
MDCK Permeability:	1.1064796126447618e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.713
Plasma Protein Binding (PPB):	90.94652557373047%
Volume Distribution (VD):	0.616
Pgp-substrate:	3.8307971954345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.42
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	5.072
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.716
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.748
Carcinogencity:	0.38
Eye Corrosion:	0.023
Eye Irritation:	0.028
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC271980

Natural Product ID:	NPC271980
*Common Name:**	YNRJWLCUSNZCQL-CQRFSKKRSA-N
IUPAC Name:	n.a.
Synonyms:	15Alpha-Hydroxymollic Acid
Standard InCHIKey:	YNRJWLCUSNZCQL-CQRFSKKRSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-17(2)8-7-9-18(3)19-14-23(32)28(6)21-11-10-20-27(5,25(34)35)22(31)15-24(33)30(20)16-29(21,30)13-12-26(19,28)4/h8,18-24,31-33H,7,9-16H2,1-6H3,(H,34,35)/t18-,19-,20+,21+,22+,23+,24+,26-,27+,28-,29+,30-/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1C[C@@H]([C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)([C@H](C[C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)C(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468878
PubChem CID:	11005454
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO19294	Acalypha communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088430]
NPO18030	Herba acalyphae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19294	Acalypha communis	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[531343]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[531343]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	32.0	ug.mL-1	PMID[531343]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[531343]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	64.0	ug.mL-1	PMID[531343]

☑ 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 NPC271980 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	209
0.1-0.2	1451
0.2-0.3	5385
0.3-0.4	12012
0.4-0.5	9725
0.5-0.6	5742
0.6-0.7	5477
0.7-0.8	2463
0.8-0.85	202
0.85-0.9	19
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193934
0.9485	High Similarity	NPC312900
0.9468	High Similarity	NPC234564
0.9362	High Similarity	NPC288906
0.9362	High Similarity	NPC263135
0.9192	High Similarity	NPC201763
0.901	High Similarity	NPC263729
0.898	High Similarity	NPC94906
0.898	High Similarity	NPC37047
0.898	High Similarity	NPC180733
0.898	High Similarity	NPC41971
0.8947	High Similarity	NPC477855
0.8922	High Similarity	NPC163216
0.8889	High Similarity	NPC71706
0.8878	High Similarity	NPC472028
0.8866	High Similarity	NPC327788
0.8866	High Similarity	NPC173272
0.8835	High Similarity	NPC285298
0.8835	High Similarity	NPC257082
0.88	High Similarity	NPC124544
0.8763	High Similarity	NPC48330
0.8763	High Similarity	NPC266431
0.8723	High Similarity	NPC146937
0.87	High Similarity	NPC75941
0.8687	High Similarity	NPC119036
0.8687	High Similarity	NPC477854
0.8673	High Similarity	NPC477853
0.8632	High Similarity	NPC474704
0.8632	High Similarity	NPC475921
0.8586	High Similarity	NPC190554
0.8571	High Similarity	NPC279974
0.8557	High Similarity	NPC470376
0.8557	High Similarity	NPC470375
0.8544	High Similarity	NPC231530
0.8544	High Similarity	NPC278628
0.8529	High Similarity	NPC470310
0.8519	High Similarity	NPC72772
0.8519	High Similarity	NPC469794
0.8511	High Similarity	NPC302111
0.8454	Intermediate Similarity	NPC211403
0.8454	Intermediate Similarity	NPC198242
0.8447	Intermediate Similarity	NPC29705
0.8438	Intermediate Similarity	NPC128496
0.8438	Intermediate Similarity	NPC213832
0.8438	Intermediate Similarity	NPC57954
0.8431	Intermediate Similarity	NPC76866
0.8431	Intermediate Similarity	NPC214946
0.8431	Intermediate Similarity	NPC148628
0.8431	Intermediate Similarity	NPC286519
0.8431	Intermediate Similarity	NPC88203
0.8431	Intermediate Similarity	NPC246736
0.8431	Intermediate Similarity	NPC304832
0.8421	Intermediate Similarity	NPC134197
0.8421	Intermediate Similarity	NPC474684
0.8421	Intermediate Similarity	NPC142361
0.8416	Intermediate Similarity	NPC15390
0.8416	Intermediate Similarity	NPC108371
0.84	Intermediate Similarity	NPC469810
0.8384	Intermediate Similarity	NPC205173
0.8381	Intermediate Similarity	NPC94529
0.8381	Intermediate Similarity	NPC211224
0.8367	Intermediate Similarity	NPC244356
0.8367	Intermediate Similarity	NPC206810
0.8367	Intermediate Similarity	NPC224060
0.8365	Intermediate Similarity	NPC295366
0.8365	Intermediate Similarity	NPC265127
0.8365	Intermediate Similarity	NPC37600
0.835	Intermediate Similarity	NPC140723
0.8333	Intermediate Similarity	NPC289148
0.8333	Intermediate Similarity	NPC477051
0.8333	Intermediate Similarity	NPC46848
0.8333	Intermediate Similarity	NPC289670
0.8333	Intermediate Similarity	NPC471900
0.8333	Intermediate Similarity	NPC52634
0.8333	Intermediate Similarity	NPC163963
0.8333	Intermediate Similarity	NPC211162
0.8333	Intermediate Similarity	NPC52899
0.8333	Intermediate Similarity	NPC121218
0.8333	Intermediate Similarity	NPC193360
0.8333	Intermediate Similarity	NPC253886
0.8333	Intermediate Similarity	NPC183374
0.8333	Intermediate Similarity	NPC477052
0.8333	Intermediate Similarity	NPC477053
0.8317	Intermediate Similarity	NPC114274
0.83	Intermediate Similarity	NPC476327
0.83	Intermediate Similarity	NPC329910
0.83	Intermediate Similarity	NPC49371
0.83	Intermediate Similarity	NPC195366
0.83	Intermediate Similarity	NPC114743
0.83	Intermediate Similarity	NPC476318
0.8286	Intermediate Similarity	NPC220974
0.8283	Intermediate Similarity	NPC111015
0.8283	Intermediate Similarity	NPC159365
0.8283	Intermediate Similarity	NPC209662
0.8283	Intermediate Similarity	NPC289539
0.8283	Intermediate Similarity	NPC215271
0.8283	Intermediate Similarity	NPC470385
0.8283	Intermediate Similarity	NPC470386
0.8283	Intermediate Similarity	NPC153775
0.8283	Intermediate Similarity	NPC261333
0.8283	Intermediate Similarity	NPC29247
0.8283	Intermediate Similarity	NPC91772
0.8283	Intermediate Similarity	NPC104371
0.8283	Intermediate Similarity	NPC292374
0.8283	Intermediate Similarity	NPC474529
0.8283	Intermediate Similarity	NPC129004
0.8283	Intermediate Similarity	NPC111524
0.8283	Intermediate Similarity	NPC101233
0.8269	Intermediate Similarity	NPC471293
0.8269	Intermediate Similarity	NPC477812
0.8265	Intermediate Similarity	NPC966
0.8265	Intermediate Similarity	NPC155120
0.8265	Intermediate Similarity	NPC23434
0.8265	Intermediate Similarity	NPC475708
0.8265	Intermediate Similarity	NPC228784
0.8265	Intermediate Similarity	NPC189520
0.8265	Intermediate Similarity	NPC288833
0.8265	Intermediate Similarity	NPC324341
0.8265	Intermediate Similarity	NPC282616
0.8252	Intermediate Similarity	NPC170615
0.8252	Intermediate Similarity	NPC22388
0.8252	Intermediate Similarity	NPC275990
0.8252	Intermediate Similarity	NPC477054
0.8247	Intermediate Similarity	NPC24705
0.8247	Intermediate Similarity	NPC56962
0.8241	Intermediate Similarity	NPC71348
0.8235	Intermediate Similarity	NPC477521
0.8235	Intermediate Similarity	NPC110149
0.8235	Intermediate Similarity	NPC287676
0.8235	Intermediate Similarity	NPC218383
0.8235	Intermediate Similarity	NPC83709
0.8229	Intermediate Similarity	NPC96496
0.8229	Intermediate Similarity	NPC269360
0.8229	Intermediate Similarity	NPC233836
0.8229	Intermediate Similarity	NPC264005
0.8229	Intermediate Similarity	NPC187376
0.8229	Intermediate Similarity	NPC159046
0.8218	Intermediate Similarity	NPC108078
0.8218	Intermediate Similarity	NPC253586
0.8218	Intermediate Similarity	NPC156546
0.8218	Intermediate Similarity	NPC170978
0.8214	Intermediate Similarity	NPC184555
0.82	Intermediate Similarity	NPC470232
0.82	Intermediate Similarity	NPC472485
0.82	Intermediate Similarity	NPC162001
0.82	Intermediate Similarity	NPC473240
0.82	Intermediate Similarity	NPC88310
0.82	Intermediate Similarity	NPC222845
0.82	Intermediate Similarity	NPC266899
0.82	Intermediate Similarity	NPC470229
0.82	Intermediate Similarity	NPC469599
0.82	Intermediate Similarity	NPC45324
0.8191	Intermediate Similarity	NPC113978
0.819	Intermediate Similarity	NPC196528
0.8182	Intermediate Similarity	NPC473690
0.8182	Intermediate Similarity	NPC181594
0.8182	Intermediate Similarity	NPC287118
0.8182	Intermediate Similarity	NPC144739
0.8182	Intermediate Similarity	NPC471902
0.8173	Intermediate Similarity	NPC469985
0.8173	Intermediate Similarity	NPC117185
0.8173	Intermediate Similarity	NPC222153
0.8173	Intermediate Similarity	NPC87927
0.8173	Intermediate Similarity	NPC191892
0.8165	Intermediate Similarity	NPC202889
0.8163	Intermediate Similarity	NPC86372
0.8163	Intermediate Similarity	NPC172361
0.8163	Intermediate Similarity	NPC169933
0.8163	Intermediate Similarity	NPC471896
0.8155	Intermediate Similarity	NPC472924
0.8155	Intermediate Similarity	NPC295276
0.8155	Intermediate Similarity	NPC471790
0.8148	Intermediate Similarity	NPC470281
0.8148	Intermediate Similarity	NPC270586
0.8144	Intermediate Similarity	NPC242864
0.8144	Intermediate Similarity	NPC328313
0.8144	Intermediate Similarity	NPC53911
0.8137	Intermediate Similarity	NPC98837
0.8137	Intermediate Similarity	NPC300179
0.8137	Intermediate Similarity	NPC102426
0.8137	Intermediate Similarity	NPC38296
0.8137	Intermediate Similarity	NPC28864
0.8137	Intermediate Similarity	NPC471038
0.8137	Intermediate Similarity	NPC78427
0.8137	Intermediate Similarity	NPC191565
0.8137	Intermediate Similarity	NPC16911
0.8137	Intermediate Similarity	NPC20479
0.8137	Intermediate Similarity	NPC38471
0.8137	Intermediate Similarity	NPC162459
0.8137	Intermediate Similarity	NPC474793
0.8125	Intermediate Similarity	NPC201273
0.8125	Intermediate Similarity	NPC80590
0.8125	Intermediate Similarity	NPC2783
0.8125	Intermediate Similarity	NPC28252
0.8125	Intermediate Similarity	NPC155011
0.8125	Intermediate Similarity	NPC55309
0.8119	Intermediate Similarity	NPC120708
0.8119	Intermediate Similarity	NPC13949
0.8119	Intermediate Similarity	NPC29152
0.8119	Intermediate Similarity	NPC470387

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 NPC271980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1736
0.2-0.3	4121
0.3-0.4	2081
0.4-0.5	545
0.5-0.6	181
0.6-0.7	172
0.7-0.8	139
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD6402	Approved
0.819	Intermediate Similarity	NPD7128	Approved
0.819	Intermediate Similarity	NPD6675	Approved
0.819	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD5328	Approved
0.8039	Intermediate Similarity	NPD4755	Approved
0.8037	Intermediate Similarity	NPD7320	Approved
0.8037	Intermediate Similarity	NPD6899	Approved
0.8037	Intermediate Similarity	NPD6881	Approved
0.8021	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6373	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.7961	Intermediate Similarity	NPD7638	Approved
0.7944	Intermediate Similarity	NPD5697	Approved
0.7944	Intermediate Similarity	NPD5701	Approved
0.79	Intermediate Similarity	NPD6079	Approved
0.789	Intermediate Similarity	NPD4634	Approved
0.789	Intermediate Similarity	NPD7102	Approved
0.789	Intermediate Similarity	NPD6883	Approved
0.789	Intermediate Similarity	NPD7290	Approved
0.7885	Intermediate Similarity	NPD5286	Approved
0.7885	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD7639	Approved
0.7885	Intermediate Similarity	NPD4700	Approved
0.7885	Intermediate Similarity	NPD4696	Approved
0.7885	Intermediate Similarity	NPD5285	Approved
0.7818	Intermediate Similarity	NPD8130	Phase 1
0.7818	Intermediate Similarity	NPD6869	Approved
0.7818	Intermediate Similarity	NPD6649	Approved
0.7818	Intermediate Similarity	NPD6617	Approved
0.7818	Intermediate Similarity	NPD6847	Approved
0.7818	Intermediate Similarity	NPD6650	Approved
0.7798	Intermediate Similarity	NPD6013	Approved
0.7798	Intermediate Similarity	NPD6012	Approved
0.7798	Intermediate Similarity	NPD6014	Approved
0.7748	Intermediate Similarity	NPD6882	Approved
0.7748	Intermediate Similarity	NPD8297	Approved
0.7739	Intermediate Similarity	NPD6319	Approved
0.7736	Intermediate Similarity	NPD4633	Approved
0.7736	Intermediate Similarity	NPD5225	Approved
0.7736	Intermediate Similarity	NPD5224	Approved
0.7736	Intermediate Similarity	NPD5211	Phase 2
0.7736	Intermediate Similarity	NPD5226	Approved
0.7732	Intermediate Similarity	NPD4786	Approved
0.7723	Intermediate Similarity	NPD7515	Phase 2
0.7706	Intermediate Similarity	NPD6011	Approved
0.7692	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD6083	Phase 2
0.7685	Intermediate Similarity	NPD6008	Approved
0.7679	Intermediate Similarity	NPD4632	Approved
0.7667	Intermediate Similarity	NPD7319	Approved
0.7664	Intermediate Similarity	NPD5174	Approved
0.7664	Intermediate Similarity	NPD5175	Approved
0.766	Intermediate Similarity	NPD6118	Approved
0.766	Intermediate Similarity	NPD6114	Approved
0.766	Intermediate Similarity	NPD6115	Approved
0.766	Intermediate Similarity	NPD6697	Approved
0.7658	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4202	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7642	Intermediate Similarity	NPD5223	Approved
0.7627	Intermediate Similarity	NPD7492	Approved
0.7596	Intermediate Similarity	NPD5222	Approved
0.7596	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD4697	Phase 3
0.7596	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5141	Approved
0.7586	Intermediate Similarity	NPD6059	Approved
0.7586	Intermediate Similarity	NPD6054	Approved
0.7583	Intermediate Similarity	NPD7736	Approved
0.7576	Intermediate Similarity	NPD3618	Phase 1
0.7563	Intermediate Similarity	NPD6616	Approved
0.7551	Intermediate Similarity	NPD3665	Phase 1
0.7551	Intermediate Similarity	NPD3666	Approved
0.7551	Intermediate Similarity	NPD3133	Approved
0.7549	Intermediate Similarity	NPD8035	Phase 2
0.7549	Intermediate Similarity	NPD8034	Phase 2
0.7542	Intermediate Similarity	NPD7604	Phase 2
0.7526	Intermediate Similarity	NPD3667	Approved
0.7525	Intermediate Similarity	NPD4753	Phase 2
0.7524	Intermediate Similarity	NPD5173	Approved
0.7523	Intermediate Similarity	NPD4767	Approved
0.7523	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7478	Intermediate Similarity	NPD6009	Approved
0.7458	Intermediate Similarity	NPD6370	Approved
0.7447	Intermediate Similarity	NPD6117	Approved
0.7426	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7507	Approved
0.7404	Intermediate Similarity	NPD7748	Approved
0.74	Intermediate Similarity	NPD6684	Approved
0.74	Intermediate Similarity	NPD7334	Approved
0.74	Intermediate Similarity	NPD7146	Approved
0.74	Intermediate Similarity	NPD7521	Approved
0.74	Intermediate Similarity	NPD6409	Approved
0.74	Intermediate Similarity	NPD5330	Approved
0.7391	Intermediate Similarity	NPD6274	Approved
0.7387	Intermediate Similarity	NPD4729	Approved
0.7387	Intermediate Similarity	NPD5128	Approved
0.7387	Intermediate Similarity	NPD4730	Approved
0.7379	Intermediate Similarity	NPD6411	Approved
0.7379	Intermediate Similarity	NPD7637	Suspended
0.7373	Intermediate Similarity	NPD6015	Approved
0.7373	Intermediate Similarity	NPD6016	Approved
0.7368	Intermediate Similarity	NPD6116	Phase 1
0.735	Intermediate Similarity	NPD7101	Approved
0.735	Intermediate Similarity	NPD7100	Approved
0.7333	Intermediate Similarity	NPD5695	Phase 3
0.7328	Intermediate Similarity	NPD7115	Discovery
0.7311	Intermediate Similarity	NPD5988	Approved
0.729	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD4788	Approved
0.7265	Intermediate Similarity	NPD6335	Approved
0.7257	Intermediate Similarity	NPD5248	Approved
0.7257	Intermediate Similarity	NPD5247	Approved
0.7257	Intermediate Similarity	NPD5249	Phase 3
0.7257	Intermediate Similarity	NPD5251	Approved
0.7257	Intermediate Similarity	NPD5250	Approved
0.7255	Intermediate Similarity	NPD6903	Approved
0.7248	Intermediate Similarity	NPD7632	Discontinued
0.7234	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5983	Phase 2
0.7227	Intermediate Similarity	NPD6908	Approved
0.7227	Intermediate Similarity	NPD6909	Approved
0.7196	Intermediate Similarity	NPD7902	Approved
0.7193	Intermediate Similarity	NPD5216	Approved
0.7193	Intermediate Similarity	NPD5217	Approved
0.7193	Intermediate Similarity	NPD5215	Approved
0.7184	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6101	Approved
0.7179	Intermediate Similarity	NPD6317	Approved
0.7172	Intermediate Similarity	NPD4221	Approved
0.7172	Intermediate Similarity	NPD4223	Phase 3
0.717	Intermediate Similarity	NPD4629	Approved
0.717	Intermediate Similarity	NPD5210	Approved
0.7158	Intermediate Similarity	NPD3703	Phase 2
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5368	Approved
0.7131	Intermediate Similarity	NPD6336	Discontinued
0.7129	Intermediate Similarity	NPD5329	Approved
0.7119	Intermediate Similarity	NPD6314	Approved
0.7119	Intermediate Similarity	NPD6313	Approved
0.7105	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5135	Approved
0.7105	Intermediate Similarity	NPD5169	Approved
0.7094	Intermediate Similarity	NPD6868	Approved
0.7087	Intermediate Similarity	NPD5737	Approved
0.7087	Intermediate Similarity	NPD6672	Approved
0.7083	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6001	Approved
0.7059	Intermediate Similarity	NPD6098	Approved
0.7048	Intermediate Similarity	NPD5284	Approved
0.7048	Intermediate Similarity	NPD5281	Approved
0.7043	Intermediate Similarity	NPD5127	Approved
0.703	Intermediate Similarity	NPD3668	Phase 3
0.703	Intermediate Similarity	NPD4197	Approved
0.7019	Intermediate Similarity	NPD6673	Approved
0.7019	Intermediate Similarity	NPD6080	Approved
0.7019	Intermediate Similarity	NPD6904	Approved
0.7016	Intermediate Similarity	NPD6033	Approved
0.7	Intermediate Similarity	NPD6435	Approved
0.6983	Remote Similarity	NPD6053	Discontinued
0.6979	Remote Similarity	NPD7339	Approved
0.6979	Remote Similarity	NPD6942	Approved
0.6975	Remote Similarity	NPD7328	Approved
0.6975	Remote Similarity	NPD7327	Approved
0.6967	Remote Similarity	NPD8328	Phase 3
0.6942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5168	Approved
0.6917	Remote Similarity	NPD7516	Approved
0.6916	Remote Similarity	NPD7900	Approved
0.6916	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5369	Approved
0.6893	Remote Similarity	NPD4690	Approved
0.6893	Remote Similarity	NPD4688	Approved
0.6893	Remote Similarity	NPD4689	Approved
0.6893	Remote Similarity	NPD5786	Approved
0.6893	Remote Similarity	NPD4138	Approved
0.6893	Remote Similarity	NPD5205	Approved
0.6893	Remote Similarity	NPD4693	Phase 3
0.6893	Remote Similarity	NPD5279	Phase 3
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6929	Approved
0.6869	Remote Similarity	NPD7645	Phase 2
0.6864	Remote Similarity	NPD5167	Approved
0.6842	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4269	Approved
0.6832	Remote Similarity	NPD4270	Approved
0.6827	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4225	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