NPASS Compound

Structure

CID190554 OpenBabel06191715572D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.7177 2.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1818 3.7733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2389 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7342 -0.5910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -1.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8466 -1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3840 -2.9296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 1.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5379 1.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3838 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6935 2.9285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 1.9526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5380 0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5377 0.4874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3840 -0.9769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2295 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 0.0004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8464 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2295 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8461 0.4882 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 -0.8466 1.4649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1086 2.6451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5378 1.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2446 -0.2199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1036 -2.9461 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 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 27 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 19 30 1 1 0 0 0 20 24 1 0 0 0 0 20 32 1 1 0 0 0 21 25 1 0 0 0 0 21 33 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 26 1 0 0 0 0 23 34 2 0 0 0 0 24 28 1 6 0 0 0 25 29 1 1 0 0 0 25 30 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	4.423
LogD:	4.132
LogS:	-4.727
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	5.284
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:	-5.011
MDCK Permeability:	7.366091267613228e-06
Pgp-inhibitor:	0.833
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.754
Plasma Protein Binding (PPB):	89.50432586669922%
Volume Distribution (VD):	0.871
Pgp-substrate:	6.080494403839111%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.464
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	8.634
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.832
Maximum Recommended Daily Dose:	0.724
Skin Sensitization:	0.277
Carcinogencity:	0.387
Eye Corrosion:	0.12
Eye Irritation:	0.099
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC190554

Natural Product ID:	NPC190554
*Common Name:**	Rubiarbonone B
IUPAC Name:	(1R,3S,3aR,5aS,5bS,6S,7aR,11aS,13aR,13bR)-1,6-dihydroxy-3a-(hydroxymethyl)-5a,8,8,11a,13a-pentamethyl-3-propan-2-yl-2,3,4,5,5b,6,7,7a,10,11,13,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:
Standard InCHIKey:	BNCWPGHWXAEYNK-MEKJSECDSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-17(2)19-14-21(33)25-29(7)11-8-18-24(28(29,6)12-13-30(19,25)16-31)20(32)15-22-26(3,4)23(34)9-10-27(18,22)5/h8,17,19-22,24-25,31-33H,9-16H2,1-7H3/t19-,20-,21+,22-,24-,25+,27+,28-,29+,30+/m0/s1
SMILES:	CC(C)[C@@H]1C[C@H]([C@@H]2[C@@]3(C)CC=C4[C@@H]([C@H](C[C@H]5C(C)(C)C(=O)CC[C@]45C)O)[C@]3(C)CC[C@@]12CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511777
PubChem CID:	44566782
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
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350148]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762798]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21044847]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	root	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	-13.7	%	PMID[500683]
NPT2	Others	Unspecified	Inhibition	=	-9.7	%	PMID[500683]
NPT2	Others	Unspecified	Inhibition	=	4.3	%	PMID[500683]
NPT2	Others	Unspecified	Inhibition	=	16.9	%	PMID[500683]
NPT2	Others	Unspecified	Inhibition	=	19.7	%	PMID[500683]

☑ 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 NPC190554 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	200
0.1-0.2	1353
0.2-0.3	4984
0.3-0.4	12318
0.4-0.5	9848
0.5-0.6	5572
0.6-0.7	4978
0.7-0.8	3022
0.8-0.85	325
0.85-0.9	90
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC15390
0.9278	High Similarity	NPC231530
0.9278	High Similarity	NPC278628
0.9239	High Similarity	NPC111015
0.9158	High Similarity	NPC83709
0.9091	High Similarity	NPC94529
0.9043	High Similarity	NPC173272
0.8936	High Similarity	NPC472485
0.8936	High Similarity	NPC48330
0.8901	High Similarity	NPC193360
0.8889	High Similarity	NPC24277
0.8878	High Similarity	NPC191892
0.8854	High Similarity	NPC477854
0.8842	High Similarity	NPC49371
0.8842	High Similarity	NPC477853
0.883	High Similarity	NPC245972
0.883	High Similarity	NPC196485
0.8804	High Similarity	NPC186688
0.88	High Similarity	NPC220229
0.88	High Similarity	NPC475060
0.8763	High Similarity	NPC154072
0.8763	High Similarity	NPC110149
0.875	High Similarity	NPC18509
0.8737	High Similarity	NPC127063
0.8737	High Similarity	NPC473240
0.8725	High Similarity	NPC197428
0.8723	High Similarity	NPC206810
0.8723	High Similarity	NPC470376
0.8723	High Similarity	NPC470375
0.8713	High Similarity	NPC217201
0.871	High Similarity	NPC100313
0.87	High Similarity	NPC296945
0.87	High Similarity	NPC85829
0.87	High Similarity	NPC202167
0.87	High Similarity	NPC260268
0.87	High Similarity	NPC150531
0.87	High Similarity	NPC49958
0.87	High Similarity	NPC302607
0.87	High Similarity	NPC149047
0.87	High Similarity	NPC152695
0.87	High Similarity	NPC476027
0.87	High Similarity	NPC97202
0.87	High Similarity	NPC214264
0.87	High Similarity	NPC48733
0.87	High Similarity	NPC319077
0.87	High Similarity	NPC171137
0.87	High Similarity	NPC50692
0.8696	High Similarity	NPC53911
0.8696	High Similarity	NPC328539
0.8696	High Similarity	NPC328313
0.8687	High Similarity	NPC140723
0.8667	High Similarity	NPC209802
0.8667	High Similarity	NPC124172
0.8667	High Similarity	NPC82902
0.8667	High Similarity	NPC221758
0.8667	High Similarity	NPC59453
0.866	High Similarity	NPC114274
0.8646	High Similarity	NPC476318
0.8646	High Similarity	NPC476327
0.8632	High Similarity	NPC471207
0.8632	High Similarity	NPC280804
0.8627	High Similarity	NPC11710
0.8617	High Similarity	NPC185936
0.8617	High Similarity	NPC272746
0.8617	High Similarity	NPC168027
0.8614	High Similarity	NPC83744
0.8614	High Similarity	NPC165873
0.8602	High Similarity	NPC275740
0.8602	High Similarity	NPC31985
0.8602	High Similarity	NPC105495
0.8602	High Similarity	NPC76879
0.8602	High Similarity	NPC32830
0.8602	High Similarity	NPC1015
0.8602	High Similarity	NPC477943
0.8602	High Similarity	NPC474245
0.8602	High Similarity	NPC86319
0.86	High Similarity	NPC209502
0.86	High Similarity	NPC75531
0.86	High Similarity	NPC29705
0.86	High Similarity	NPC149124
0.86	High Similarity	NPC204833
0.86	High Similarity	NPC477812
0.8587	High Similarity	NPC475740
0.8587	High Similarity	NPC317590
0.8586	High Similarity	NPC185530
0.8586	High Similarity	NPC193934
0.8586	High Similarity	NPC271980
0.8571	High Similarity	NPC474218
0.8571	High Similarity	NPC144956
0.8571	High Similarity	NPC218383
0.8557	High Similarity	NPC189880
0.8557	High Similarity	NPC108078
0.8556	High Similarity	NPC110778
0.8556	High Similarity	NPC476082
0.8556	High Similarity	NPC278648
0.8542	High Similarity	NPC469599
0.8529	High Similarity	NPC329417
0.8526	High Similarity	NPC475255
0.8526	High Similarity	NPC244356
0.8526	High Similarity	NPC477855
0.8526	High Similarity	NPC224060
0.8515	High Similarity	NPC475571
0.8511	High Similarity	NPC171441
0.8511	High Similarity	NPC85173
0.85	High Similarity	NPC26478
0.85	High Similarity	NPC117185
0.8495	Intermediate Similarity	NPC131470
0.8495	Intermediate Similarity	NPC143767
0.8495	Intermediate Similarity	NPC470542
0.8495	Intermediate Similarity	NPC471722
0.8478	Intermediate Similarity	NPC51014
0.8478	Intermediate Similarity	NPC474732
0.8478	Intermediate Similarity	NPC474778
0.8478	Intermediate Similarity	NPC31564
0.8478	Intermediate Similarity	NPC145879
0.8478	Intermediate Similarity	NPC469994
0.8478	Intermediate Similarity	NPC20688
0.8478	Intermediate Similarity	NPC474733
0.8469	Intermediate Similarity	NPC58942
0.8469	Intermediate Similarity	NPC260149
0.8462	Intermediate Similarity	NPC475798
0.8462	Intermediate Similarity	NPC127606
0.8454	Intermediate Similarity	NPC5532
0.8454	Intermediate Similarity	NPC304899
0.8454	Intermediate Similarity	NPC253115
0.8454	Intermediate Similarity	NPC469545
0.8454	Intermediate Similarity	NPC61369
0.8444	Intermediate Similarity	NPC151519
0.8444	Intermediate Similarity	NPC470614
0.8444	Intermediate Similarity	NPC1272
0.8438	Intermediate Similarity	NPC209662
0.8438	Intermediate Similarity	NPC191094
0.8438	Intermediate Similarity	NPC166906
0.8438	Intermediate Similarity	NPC302008
0.8431	Intermediate Similarity	NPC144459
0.8431	Intermediate Similarity	NPC477916
0.8421	Intermediate Similarity	NPC23434
0.8421	Intermediate Similarity	NPC476168
0.8421	Intermediate Similarity	NPC154101
0.8416	Intermediate Similarity	NPC137657
0.8404	Intermediate Similarity	NPC474704
0.8404	Intermediate Similarity	NPC69627
0.8404	Intermediate Similarity	NPC475921
0.84	Intermediate Similarity	NPC473424
0.84	Intermediate Similarity	NPC22388
0.84	Intermediate Similarity	NPC477915
0.8387	Intermediate Similarity	NPC58063
0.8387	Intermediate Similarity	NPC472495
0.8387	Intermediate Similarity	NPC73064
0.8387	Intermediate Similarity	NPC153604
0.8387	Intermediate Similarity	NPC57469
0.8387	Intermediate Similarity	NPC474684
0.8387	Intermediate Similarity	NPC298904
0.8387	Intermediate Similarity	NPC142361
0.8387	Intermediate Similarity	NPC4643
0.8381	Intermediate Similarity	NPC71348
0.837	Intermediate Similarity	NPC470574
0.837	Intermediate Similarity	NPC133954
0.837	Intermediate Similarity	NPC197823
0.837	Intermediate Similarity	NPC202868
0.837	Intermediate Similarity	NPC469948
0.8367	Intermediate Similarity	NPC170978
0.8352	Intermediate Similarity	NPC477818
0.8352	Intermediate Similarity	NPC475726
0.8352	Intermediate Similarity	NPC193870
0.8352	Intermediate Similarity	NPC141941
0.8352	Intermediate Similarity	NPC472743
0.8351	Intermediate Similarity	NPC45324
0.8351	Intermediate Similarity	NPC138245
0.8351	Intermediate Similarity	NPC279974
0.8351	Intermediate Similarity	NPC222845
0.8351	Intermediate Similarity	NPC231060
0.8351	Intermediate Similarity	NPC271195
0.8351	Intermediate Similarity	NPC139570
0.8351	Intermediate Similarity	NPC473170
0.8351	Intermediate Similarity	NPC317586
0.8351	Intermediate Similarity	NPC470016
0.8351	Intermediate Similarity	NPC472932
0.8351	Intermediate Similarity	NPC84018
0.8351	Intermediate Similarity	NPC162001
0.8351	Intermediate Similarity	NPC200702
0.835	Intermediate Similarity	NPC65941
0.8333	Intermediate Similarity	NPC12722
0.8333	Intermediate Similarity	NPC257353
0.8333	Intermediate Similarity	NPC181594
0.8333	Intermediate Similarity	NPC144739
0.8333	Intermediate Similarity	NPC69454
0.8333	Intermediate Similarity	NPC60681
0.8317	Intermediate Similarity	NPC312900
0.8317	Intermediate Similarity	NPC55872
0.8316	Intermediate Similarity	NPC183283
0.8316	Intermediate Similarity	NPC136801
0.8316	Intermediate Similarity	NPC48010
0.8316	Intermediate Similarity	NPC126993
0.8316	Intermediate Similarity	NPC320026
0.8316	Intermediate Similarity	NPC80401
0.8302	Intermediate Similarity	NPC108721
0.8302	Intermediate Similarity	NPC73300
0.8302	Intermediate Similarity	NPC202889
0.83	Intermediate Similarity	NPC474327

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 NPC190554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1596
0.2-0.3	4092
0.3-0.4	2235
0.4-0.5	570
0.5-0.6	169
0.6-0.7	136
0.7-0.8	146
0.8-0.85	36
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8804	High Similarity	NPD5328	Approved
0.875	High Similarity	NPD4755	Approved
0.8667	High Similarity	NPD4786	Approved
0.8617	High Similarity	NPD6079	Approved
0.8571	High Similarity	NPD4696	Approved
0.8571	High Similarity	NPD5286	Approved
0.8571	High Similarity	NPD5285	Approved
0.8571	High Similarity	NPD4700	Approved
0.8526	High Similarity	NPD4202	Approved
0.8485	Intermediate Similarity	NPD5223	Approved
0.8444	Intermediate Similarity	NPD3667	Approved
0.84	Intermediate Similarity	NPD4633	Approved
0.84	Intermediate Similarity	NPD5225	Approved
0.84	Intermediate Similarity	NPD5224	Approved
0.84	Intermediate Similarity	NPD5226	Approved
0.84	Intermediate Similarity	NPD5211	Phase 2
0.8333	Intermediate Similarity	NPD6402	Approved
0.8333	Intermediate Similarity	NPD7128	Approved
0.8333	Intermediate Similarity	NPD6675	Approved
0.8333	Intermediate Similarity	NPD5739	Approved
0.8317	Intermediate Similarity	NPD5175	Approved
0.8317	Intermediate Similarity	NPD4754	Approved
0.8317	Intermediate Similarity	NPD5174	Approved
0.828	Intermediate Similarity	NPD3618	Phase 1
0.8265	Intermediate Similarity	NPD5221	Approved
0.8265	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8265	Intermediate Similarity	NPD5222	Approved
0.8265	Intermediate Similarity	NPD4697	Phase 3
0.8261	Intermediate Similarity	NPD3133	Approved
0.8261	Intermediate Similarity	NPD3665	Phase 1
0.8261	Intermediate Similarity	NPD3666	Approved
0.8235	Intermediate Similarity	NPD5141	Approved
0.819	Intermediate Similarity	NPD4634	Approved
0.8182	Intermediate Similarity	NPD5173	Approved
0.8173	Intermediate Similarity	NPD6899	Approved
0.8173	Intermediate Similarity	NPD6881	Approved
0.8173	Intermediate Similarity	NPD7320	Approved
0.8155	Intermediate Similarity	NPD4768	Approved
0.8155	Intermediate Similarity	NPD4767	Approved
0.8144	Intermediate Similarity	NPD6399	Phase 3
0.8095	Intermediate Similarity	NPD6372	Approved
0.8095	Intermediate Similarity	NPD6373	Approved
0.8077	Intermediate Similarity	NPD5701	Approved
0.8077	Intermediate Similarity	NPD5697	Approved
0.8041	Intermediate Similarity	NPD7515	Phase 2
0.8022	Intermediate Similarity	NPD7525	Registered
0.8021	Intermediate Similarity	NPD4753	Phase 2
0.8019	Intermediate Similarity	NPD7290	Approved
0.8019	Intermediate Similarity	NPD6883	Approved
0.8019	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD5128	Approved
0.8	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD4729	Approved
0.8	Intermediate Similarity	NPD4730	Approved
0.7981	Intermediate Similarity	NPD6008	Approved
0.7979	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4632	Approved
0.7944	Intermediate Similarity	NPD6869	Approved
0.7944	Intermediate Similarity	NPD6649	Approved
0.7944	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6847	Approved
0.7944	Intermediate Similarity	NPD6650	Approved
0.7944	Intermediate Similarity	NPD6617	Approved
0.7944	Intermediate Similarity	NPD8130	Phase 1
0.7925	Intermediate Similarity	NPD6013	Approved
0.7925	Intermediate Similarity	NPD6014	Approved
0.7925	Intermediate Similarity	NPD6012	Approved
0.7872	Intermediate Similarity	NPD3668	Phase 3
0.787	Intermediate Similarity	NPD6882	Approved
0.787	Intermediate Similarity	NPD8297	Approved
0.785	Intermediate Similarity	NPD5249	Phase 3
0.785	Intermediate Similarity	NPD5247	Approved
0.785	Intermediate Similarity	NPD5248	Approved
0.785	Intermediate Similarity	NPD5250	Approved
0.785	Intermediate Similarity	NPD5135	Approved
0.785	Intermediate Similarity	NPD5169	Approved
0.785	Intermediate Similarity	NPD5251	Approved
0.785	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4221	Approved
0.7849	Intermediate Similarity	NPD4223	Phase 3
0.7789	Intermediate Similarity	NPD5329	Approved
0.7778	Intermediate Similarity	NPD5127	Approved
0.7778	Intermediate Similarity	NPD5215	Approved
0.7778	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5217	Approved
0.7778	Intermediate Similarity	NPD5216	Approved
0.7766	Intermediate Similarity	NPD4788	Approved
0.7748	Intermediate Similarity	NPD6009	Approved
0.7745	Intermediate Similarity	NPD7638	Approved
0.7736	Intermediate Similarity	NPD6412	Phase 2
0.7732	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7748	Approved
0.7699	Intermediate Similarity	NPD6059	Approved
0.7699	Intermediate Similarity	NPD6054	Approved
0.7684	Intermediate Similarity	NPD4197	Approved
0.7677	Intermediate Similarity	NPD8035	Phase 2
0.7677	Intermediate Similarity	NPD8034	Phase 2
0.767	Intermediate Similarity	NPD7640	Approved
0.767	Intermediate Similarity	NPD7639	Approved
0.7667	Intermediate Similarity	NPD6942	Approved
0.7667	Intermediate Similarity	NPD7339	Approved
0.7667	Intermediate Similarity	NPD3703	Phase 2
0.7647	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD6084	Phase 2
0.7624	Intermediate Similarity	NPD4629	Approved
0.7624	Intermediate Similarity	NPD5210	Approved
0.7568	Intermediate Similarity	NPD5167	Approved
0.7565	Intermediate Similarity	NPD6370	Approved
0.7544	Intermediate Similarity	NPD6319	Approved
0.7542	Intermediate Similarity	NPD7736	Approved
0.7526	Intermediate Similarity	NPD6684	Approved
0.7526	Intermediate Similarity	NPD7334	Approved
0.7526	Intermediate Similarity	NPD5330	Approved
0.7526	Intermediate Similarity	NPD7521	Approved
0.7526	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5205	Approved
0.7526	Intermediate Similarity	NPD4689	Approved
0.7526	Intermediate Similarity	NPD6409	Approved
0.7526	Intermediate Similarity	NPD7146	Approved
0.7526	Intermediate Similarity	NPD4690	Approved
0.7526	Intermediate Similarity	NPD4688	Approved
0.7526	Intermediate Similarity	NPD4693	Phase 3
0.7526	Intermediate Similarity	NPD4138	Approved
0.7526	Intermediate Similarity	NPD5279	Phase 3
0.7522	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5168	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD6016	Approved
0.7478	Intermediate Similarity	NPD6015	Approved
0.7478	Intermediate Similarity	NPD5983	Phase 2
0.7456	Intermediate Similarity	NPD7101	Approved
0.7456	Intermediate Similarity	NPD7100	Approved
0.7449	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7492	Approved
0.7434	Intermediate Similarity	NPD6317	Approved
0.7419	Intermediate Similarity	NPD6114	Approved
0.7419	Intermediate Similarity	NPD6697	Approved
0.7419	Intermediate Similarity	NPD6115	Approved
0.7419	Intermediate Similarity	NPD6118	Approved
0.7414	Intermediate Similarity	NPD5988	Approved
0.7374	Intermediate Similarity	NPD6903	Approved
0.7373	Intermediate Similarity	NPD6336	Discontinued
0.7373	Intermediate Similarity	NPD6616	Approved
0.7373	Intermediate Similarity	NPD7507	Approved
0.7368	Intermediate Similarity	NPD6313	Approved
0.7368	Intermediate Similarity	NPD6314	Approved
0.7353	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD5280	Approved
0.7347	Intermediate Similarity	NPD5690	Phase 2
0.7347	Intermediate Similarity	NPD4694	Approved
0.734	Intermediate Similarity	NPD7645	Phase 2
0.7333	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6908	Approved
0.7328	Intermediate Similarity	NPD6909	Approved
0.7327	Intermediate Similarity	NPD5281	Approved
0.7327	Intermediate Similarity	NPD5284	Approved
0.7312	Intermediate Similarity	NPD6116	Phase 1
0.7311	Intermediate Similarity	NPD7078	Approved
0.7311	Intermediate Similarity	NPD8293	Discontinued
0.7282	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5695	Phase 3
0.725	Intermediate Similarity	NPD6033	Approved
0.7238	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD4244	Approved
0.7222	Intermediate Similarity	NPD4245	Approved
0.7204	Intermediate Similarity	NPD6117	Approved
0.72	Intermediate Similarity	NPD6672	Approved
0.72	Intermediate Similarity	NPD5737	Approved
0.7193	Intermediate Similarity	NPD6868	Approved
0.719	Intermediate Similarity	NPD7319	Approved
0.7188	Intermediate Similarity	NPD4692	Approved
0.7188	Intermediate Similarity	NPD4139	Approved
0.7179	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4785	Approved
0.7174	Intermediate Similarity	NPD4784	Approved
0.7172	Intermediate Similarity	NPD6098	Approved
0.7158	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7129	Intermediate Similarity	NPD6904	Approved
0.7129	Intermediate Similarity	NPD6673	Approved
0.7129	Intermediate Similarity	NPD6080	Approved
0.7111	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3698	Phase 2
0.7083	Intermediate Similarity	NPD4748	Discontinued
0.7083	Intermediate Similarity	NPD5368	Approved
0.7083	Intermediate Similarity	NPD4695	Discontinued
0.708	Intermediate Similarity	NPD6053	Discontinued
0.7059	Intermediate Similarity	NPD6067	Discontinued
0.7053	Intermediate Similarity	NPD3617	Approved
0.7037	Intermediate Similarity	NPD7632	Discontinued
0.699	Remote Similarity	NPD6411	Approved
0.6989	Remote Similarity	NPD6924	Approved
0.6989	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6926	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