NPASS Compound

Structure

NPC120708 OpenBabel07101719252D 41 44 0 0 1 0 0 0 0 0999 V2000 -2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.3212 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 2.9641 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 -0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 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 -1.5388 0.5000 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 -0.9511 1.3090 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 -4.1132 0.0000 C 0 0 1 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 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 0 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -4.8564 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 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 -5.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -4.6485 0.0000 O 0 0 0 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 1 19 2 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 7 33 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 20 2 1 1 0 0 0 20 22 1 0 0 0 0 21 3 1 1 0 0 0 21 30 1 0 0 0 0 22 34 1 1 0 0 0 23 24 2 0 0 0 0 23 33 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 25 32 1 1 0 0 0 26 34 1 6 0 0 0 26 35 1 0 0 0 0 27 31 1 0 0 0 0 27 41 1 6 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 29 38 2 0 0 0 0 29 41 1 0 0 0 0 30 39 2 0 0 0 0 30 40 1 0 0 0 0 32 6 1 1 0 0 0 33 34 1 6 0 0 0 34 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.37
Volume:	610.743
LogP:	5.65
LogD:	4.265
LogS:	-4.219
# Rotatable Bonds:	9
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	5.245
Fsp3:	0.794
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.813
MDCK Permeability:	7.617326446052175e-06
Pgp-inhibitor:	0.033
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.207
30% Bioavailability (F30%):	0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	95.03458404541016%
Volume Distribution (VD):	0.456
Pgp-substrate:	3.6956117153167725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	3.664
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.597
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.717
Carcinogencity:	0.273
Eye Corrosion:	0.904
Eye Irritation:	0.211
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC120708

Natural Product ID:	NPC120708
*Common Name:**	(25S)-(+)-12Alpha-Hydroxy-3Alpha-Malonyloxy-24-Methyllanosta-8,24(31)-Dien-26-Oic Acid
IUPAC Name:	(2S,6R)-6-[(3R,5R,10S,12S,13R,14S,17R)-3-(2-carboxyacetyl)oxy-12-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
Synonyms:
Standard InCHIKey:	HMOMGSPWDYKCAH-JJPOTAKPSA-N
Standard InCHI:	InChI=1S/C34H52O7/c1-19(21(3)30(39)40)9-10-20(2)22-13-16-33(7)23-11-12-25-31(4,5)27(41-29(38)18-28(36)37)14-15-32(25,6)24(23)17-26(35)34(22,33)8/h20-22,25-27,35H,1,9-18H2,2-8H3,(H,36,37)(H,39,40)/t20-,21+,22-,25+,26+,27-,32-,33+,34+/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(C[C@@H]([C@]12C)O)[C@@]1(C)CC[C@H](C(C)(C)[C@@H]1CC3)OC(=O)CC(=O)O)[C@H](C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444451
PubChem CID:	21581807
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
NPO8228	Piptoporus betulinus	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099232]
NPO8228	Piptoporus betulinus	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932134]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	65.0	%	PMID[572813]

☑ 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 NPC120708 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	180
0.1-0.2	1160
0.2-0.3	4748
0.3-0.4	12283
0.4-0.5	9874
0.5-0.6	5978
0.6-0.7	5978
0.7-0.8	2269
0.8-0.85	172
0.85-0.9	42
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC473514
0.9333	High Similarity	NPC26888
0.9326	High Similarity	NPC474889
0.9263	High Similarity	NPC473788
0.9263	High Similarity	NPC475558
0.9239	High Similarity	NPC473648
0.9222	High Similarity	NPC175628
0.9222	High Similarity	NPC111585
0.9222	High Similarity	NPC148414
0.9213	High Similarity	NPC242864
0.9032	High Similarity	NPC184848
0.9032	High Similarity	NPC69548
0.9011	High Similarity	NPC471896
0.8989	High Similarity	NPC28252
0.8989	High Similarity	NPC55309
0.898	High Similarity	NPC475494
0.8936	High Similarity	NPC327788
0.8901	High Similarity	NPC474704
0.8901	High Similarity	NPC475921
0.8889	High Similarity	NPC159046
0.8889	High Similarity	NPC233836
0.8889	High Similarity	NPC187376
0.883	High Similarity	NPC470016
0.883	High Similarity	NPC317586
0.8817	High Similarity	NPC473690
0.8817	High Similarity	NPC471902
0.8817	High Similarity	NPC287118
0.8804	High Similarity	NPC469400
0.875	High Similarity	NPC477813
0.8723	High Similarity	NPC166906
0.871	High Similarity	NPC471901
0.871	High Similarity	NPC475416
0.871	High Similarity	NPC23434
0.871	High Similarity	NPC297265
0.8696	High Similarity	NPC474570
0.8696	High Similarity	NPC77168
0.8696	High Similarity	NPC84271
0.8696	High Similarity	NPC102414
0.8681	High Similarity	NPC474684
0.8681	High Similarity	NPC142361
0.8632	High Similarity	NPC279974
0.8632	High Similarity	NPC195715
0.8632	High Similarity	NPC48330
0.8617	High Similarity	NPC470224
0.8602	High Similarity	NPC20388
0.8587	High Similarity	NPC471724
0.8571	High Similarity	NPC474970
0.8571	High Similarity	NPC155011
0.8571	High Similarity	NPC325594
0.8557	High Similarity	NPC119036
0.8542	High Similarity	NPC328162
0.8542	High Similarity	NPC305483
0.8542	High Similarity	NPC173272
0.8542	High Similarity	NPC96859
0.8526	High Similarity	NPC469406
0.8526	High Similarity	NPC159410
0.8526	High Similarity	NPC78580
0.8526	High Similarity	NPC23621
0.8526	High Similarity	NPC184006
0.8511	High Similarity	NPC189520
0.85	High Similarity	NPC96268
0.8495	Intermediate Similarity	NPC57954
0.8495	Intermediate Similarity	NPC213832
0.8485	Intermediate Similarity	NPC296879
0.8485	Intermediate Similarity	NPC471119
0.8478	Intermediate Similarity	NPC96496
0.8454	Intermediate Similarity	NPC320306
0.8438	Intermediate Similarity	NPC162001
0.8438	Intermediate Similarity	NPC45324
0.8438	Intermediate Similarity	NPC205173
0.8438	Intermediate Similarity	NPC210214
0.8438	Intermediate Similarity	NPC222845
0.8438	Intermediate Similarity	NPC23241
0.8438	Intermediate Similarity	NPC469599
0.8421	Intermediate Similarity	NPC470375
0.8421	Intermediate Similarity	NPC86368
0.8421	Intermediate Similarity	NPC170220
0.8421	Intermediate Similarity	NPC470376
0.8421	Intermediate Similarity	NPC141497
0.8421	Intermediate Similarity	NPC107674
0.8404	Intermediate Similarity	NPC44240
0.84	Intermediate Similarity	NPC159442
0.84	Intermediate Similarity	NPC55954
0.84	Intermediate Similarity	NPC218513
0.8387	Intermediate Similarity	NPC471722
0.8387	Intermediate Similarity	NPC146937
0.8387	Intermediate Similarity	NPC4309
0.8387	Intermediate Similarity	NPC183546
0.8387	Intermediate Similarity	NPC471900
0.837	Intermediate Similarity	NPC73038
0.837	Intermediate Similarity	NPC94755
0.837	Intermediate Similarity	NPC72133
0.837	Intermediate Similarity	NPC264127
0.8367	Intermediate Similarity	NPC164349
0.8351	Intermediate Similarity	NPC7124
0.8351	Intermediate Similarity	NPC328371
0.8351	Intermediate Similarity	NPC471153
0.8351	Intermediate Similarity	NPC42042
0.8333	Intermediate Similarity	NPC471720
0.8333	Intermediate Similarity	NPC474922
0.8333	Intermediate Similarity	NPC220974
0.8316	Intermediate Similarity	NPC288833
0.8316	Intermediate Similarity	NPC60755
0.8316	Intermediate Similarity	NPC228784
0.8316	Intermediate Similarity	NPC285184
0.8316	Intermediate Similarity	NPC86266
0.8316	Intermediate Similarity	NPC77099
0.8316	Intermediate Similarity	NPC212301
0.8316	Intermediate Similarity	NPC324341
0.8316	Intermediate Similarity	NPC110657
0.8316	Intermediate Similarity	NPC155120
0.8316	Intermediate Similarity	NPC282616
0.8316	Intermediate Similarity	NPC966
0.8316	Intermediate Similarity	NPC470590
0.8298	Intermediate Similarity	NPC54689
0.8298	Intermediate Similarity	NPC128496
0.8298	Intermediate Similarity	NPC1015
0.8298	Intermediate Similarity	NPC31985
0.8283	Intermediate Similarity	NPC477521
0.8283	Intermediate Similarity	NPC476299
0.8283	Intermediate Similarity	NPC474012
0.8283	Intermediate Similarity	NPC327431
0.8283	Intermediate Similarity	NPC94906
0.8283	Intermediate Similarity	NPC316964
0.828	Intermediate Similarity	NPC269360
0.828	Intermediate Similarity	NPC33768
0.828	Intermediate Similarity	NPC134197
0.828	Intermediate Similarity	NPC167877
0.828	Intermediate Similarity	NPC264005
0.8265	Intermediate Similarity	NPC43747
0.8265	Intermediate Similarity	NPC141401
0.8265	Intermediate Similarity	NPC108078
0.8265	Intermediate Similarity	NPC253586
0.8265	Intermediate Similarity	NPC26413
0.8252	Intermediate Similarity	NPC472218
0.8252	Intermediate Similarity	NPC472219
0.8252	Intermediate Similarity	NPC195708
0.8252	Intermediate Similarity	NPC472217
0.8247	Intermediate Similarity	NPC318282
0.8247	Intermediate Similarity	NPC469329
0.8247	Intermediate Similarity	NPC174948
0.8247	Intermediate Similarity	NPC30677
0.8247	Intermediate Similarity	NPC469995
0.8247	Intermediate Similarity	NPC180557
0.8247	Intermediate Similarity	NPC263347
0.8247	Intermediate Similarity	NPC37787
0.8247	Intermediate Similarity	NPC173875
0.8247	Intermediate Similarity	NPC88310
0.8247	Intermediate Similarity	NPC473415
0.8242	Intermediate Similarity	NPC471037
0.8235	Intermediate Similarity	NPC278628
0.8235	Intermediate Similarity	NPC231530
0.8229	Intermediate Similarity	NPC206810
0.8222	Intermediate Similarity	NPC473420
0.8218	Intermediate Similarity	NPC470310
0.8218	Intermediate Similarity	NPC222153
0.8211	Intermediate Similarity	NPC111110
0.8211	Intermediate Similarity	NPC113989
0.8211	Intermediate Similarity	NPC169933
0.8211	Intermediate Similarity	NPC473269
0.8211	Intermediate Similarity	NPC477149
0.8211	Intermediate Similarity	NPC477147
0.8211	Intermediate Similarity	NPC86372
0.8211	Intermediate Similarity	NPC120840
0.8211	Intermediate Similarity	NPC474728
0.8211	Intermediate Similarity	NPC470589
0.8211	Intermediate Similarity	NPC172361
0.8211	Intermediate Similarity	NPC126369
0.8208	Intermediate Similarity	NPC472926
0.82	Intermediate Similarity	NPC115899
0.82	Intermediate Similarity	NPC75941
0.8191	Intermediate Similarity	NPC143767
0.8191	Intermediate Similarity	NPC328313
0.8191	Intermediate Similarity	NPC97884
0.8191	Intermediate Similarity	NPC53911
0.8191	Intermediate Similarity	NPC294480
0.8191	Intermediate Similarity	NPC131470
0.8191	Intermediate Similarity	NPC472220
0.8182	Intermediate Similarity	NPC186810
0.8182	Intermediate Similarity	NPC48647
0.8182	Intermediate Similarity	NPC16911
0.8182	Intermediate Similarity	NPC472028
0.8182	Intermediate Similarity	NPC477854
0.8182	Intermediate Similarity	NPC78427
0.8173	Intermediate Similarity	NPC265655
0.8173	Intermediate Similarity	NPC218853
0.8173	Intermediate Similarity	NPC472216
0.8173	Intermediate Similarity	NPC284828
0.8173	Intermediate Similarity	NPC173905
0.8173	Intermediate Similarity	NPC5475
0.8172	Intermediate Similarity	NPC212843
0.8172	Intermediate Similarity	NPC2783
0.8172	Intermediate Similarity	NPC6979
0.8172	Intermediate Similarity	NPC12774
0.8163	Intermediate Similarity	NPC471777
0.8163	Intermediate Similarity	NPC98874
0.8163	Intermediate Similarity	NPC327179
0.8163	Intermediate Similarity	NPC132824
0.8163	Intermediate Similarity	NPC13949
0.8163	Intermediate Similarity	NPC95565

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 NPC120708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1551
0.2-0.3	3924
0.3-0.4	2361
0.4-0.5	640
0.5-0.6	210
0.6-0.7	210
0.7-0.8	101
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
0.8421	Intermediate Similarity	NPD6399	Phase 3
0.8152	Intermediate Similarity	NPD4786	Approved
0.8125	Intermediate Similarity	NPD8035	Phase 2
0.8125	Intermediate Similarity	NPD8034	Phase 2
0.8125	Intermediate Similarity	NPD6411	Approved
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD5739	Approved
0.8058	Intermediate Similarity	NPD6402	Approved
0.8058	Intermediate Similarity	NPD7128	Approved
0.8058	Intermediate Similarity	NPD6675	Approved
0.7959	Intermediate Similarity	NPD7748	Approved
0.7935	Intermediate Similarity	NPD3667	Approved
0.7917	Intermediate Similarity	NPD6101	Approved
0.7917	Intermediate Similarity	NPD5328	Approved
0.7917	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6899	Approved
0.7905	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7879	Intermediate Similarity	NPD5695	Phase 3
0.785	Intermediate Similarity	NPD8130	Phase 1
0.783	Intermediate Similarity	NPD6373	Approved
0.783	Intermediate Similarity	NPD6372	Approved
0.7818	Intermediate Similarity	NPD7115	Discovery
0.781	Intermediate Similarity	NPD5701	Approved
0.781	Intermediate Similarity	NPD5697	Approved
0.7789	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD8297	Approved
0.7757	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7102	Approved
0.7755	Intermediate Similarity	NPD7515	Phase 2
0.7755	Intermediate Similarity	NPD6079	Approved
0.7723	Intermediate Similarity	NPD7902	Approved
0.7685	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6649	Approved
0.7685	Intermediate Similarity	NPD6617	Approved
0.7685	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7629	Intermediate Similarity	NPD6672	Approved
0.7629	Intermediate Similarity	NPD5737	Approved
0.7615	Intermediate Similarity	NPD6882	Approved
0.7604	Intermediate Similarity	NPD6409	Approved
0.7604	Intermediate Similarity	NPD5330	Approved
0.7604	Intermediate Similarity	NPD6684	Approved
0.7604	Intermediate Similarity	NPD7521	Approved
0.7604	Intermediate Similarity	NPD7334	Approved
0.7604	Intermediate Similarity	NPD7146	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD6011	Approved
0.7549	Intermediate Similarity	NPD4755	Approved
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7476	Intermediate Similarity	NPD5696	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7451	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5222	Approved
0.7451	Intermediate Similarity	NPD5221	Approved
0.7451	Intermediate Similarity	NPD4697	Phase 3
0.7449	Intermediate Similarity	NPD6903	Approved
0.7449	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5279	Phase 3
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD7637	Suspended
0.7396	Intermediate Similarity	NPD3665	Phase 1
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7396	Intermediate Similarity	NPD3133	Approved
0.7396	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7379	Intermediate Similarity	NPD5173	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD6942	Approved
0.7363	Intermediate Similarity	NPD7339	Approved
0.7353	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7525	Registered
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7308	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7257	Intermediate Similarity	NPD6868	Approved
0.7257	Intermediate Similarity	NPD6274	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6098	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5281	Approved
0.7228	Intermediate Similarity	NPD5284	Approved
0.7228	Intermediate Similarity	NPD6050	Approved
0.7227	Intermediate Similarity	NPD8293	Discontinued
0.7222	Intermediate Similarity	NPD6008	Approved
0.7217	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7492	Approved
0.72	Intermediate Similarity	NPD6904	Approved
0.72	Intermediate Similarity	NPD6080	Approved
0.72	Intermediate Similarity	NPD6673	Approved
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7182	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5223	Approved
0.7167	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.713	Intermediate Similarity	NPD6335	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.7129	Intermediate Similarity	NPD5692	Phase 3
0.7117	Intermediate Similarity	NPD4634	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6909	Approved
0.7094	Intermediate Similarity	NPD6908	Approved
0.7083	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD7078	Approved
0.708	Intermediate Similarity	NPD4632	Approved
0.7064	Intermediate Similarity	NPD4767	Approved
0.7064	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD5694	Approved
0.7053	Intermediate Similarity	NPD7645	Phase 2
0.7043	Intermediate Similarity	NPD6317	Approved
0.7043	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4754	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7019	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD4223	Phase 3
0.701	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.6983	Remote Similarity	NPD6313	Approved
0.6983	Remote Similarity	NPD6314	Approved
0.6979	Remote Similarity	NPD4748	Discontinued
0.697	Remote Similarity	NPD5329	Approved
0.6961	Remote Similarity	NPD5207	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD6016	Approved
0.6947	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD4788	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6931	Remote Similarity	NPD5208	Approved
0.6923	Remote Similarity	NPD6001	Approved
0.6907	Remote Similarity	NPD4692	Approved
0.6907	Remote Similarity	NPD4139	Approved
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD4694	Approved
0.69	Remote Similarity	NPD5690	Phase 2
0.6897	Remote Similarity	NPD6009	Approved
0.6893	Remote Similarity	NPD5693	Phase 1
0.6891	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4197	Approved
0.6863	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6051	Approved
0.6848	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6053	Discontinued
0.6837	Remote Similarity	NPD6435	Approved
0.6837	Remote Similarity	NPD4269	Approved
0.6837	Remote Similarity	NPD4270	Approved
0.6833	Remote Similarity	NPD7604	Phase 2
0.6833	Remote Similarity	NPD8328	Phase 3
0.6832	Remote Similarity	NPD3573	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5250	Approved
0.6807	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5983	Phase 2
0.6796	Remote Similarity	NPD5785	Approved
0.6786	Remote Similarity	NPD5168	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6771	Remote Similarity	NPD3617	Approved
0.6768	Remote Similarity	NPD7154	Phase 3
0.6768	Remote Similarity	NPD6695	Phase 3
0.6754	Remote Similarity	NPD5217	Approved
0.6754	Remote Similarity	NPD5216	Approved
0.6754	Remote Similarity	NPD5215	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