NPASS Compound

Structure

CID278628 OpenBabel06191716082D 37 41 0 0 1 0 0 0 0 0999 V2000 0.7186 -2.9339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1852 -3.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2161 -4.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2482 1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7427 0.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6721 1.9705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8479 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8481 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3900 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5430 2.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 -1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5424 -1.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3898 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8483 -2.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6962 -2.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2855 -3.7060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6957 0.9790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9561 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5425 -0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5422 -0.4882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3900 0.9786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2371 2.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6955 -0.0004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8479 -0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2371 1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5430 1.4677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8476 -0.4890 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 0.8481 -1.4675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4419 -4.3606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5423 -1.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2491 0.2191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1128 2.9513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 -2.7487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 12 1 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 29 1 0 0 0 0 12 31 1 0 0 0 0 13 14 1 0 0 0 0 13 30 1 0 0 0 0 14 32 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 17 37 1 0 0 0 0 18 21 1 0 0 0 0 19 33 2 0 0 0 0 19 37 1 0 0 0 0 20 26 1 0 0 0 0 20 29 1 0 0 0 0 21 32 1 1 0 0 0 22 26 1 0 0 0 0 22 34 1 1 0 0 0 23 27 1 0 0 0 0 23 35 1 6 0 0 0 24 28 1 0 0 0 0 24 29 1 1 0 0 0 25 28 1 0 0 0 0 25 36 2 0 0 0 0 26 30 1 6 0 0 0 27 31 1 1 0 0 0 27 32 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.37
Volume:	555.287
LogP:	4.824
LogD:	4.25
LogS:	-4.998
# Rotatable Bonds:	4
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	5.273
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
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:	-5.156
MDCK Permeability:	1.2725554370263126e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	84.59517669677734%
Volume Distribution (VD):	1.004
Pgp-substrate:	9.66651439666748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.722

ADMET: Excretion

Clearance (CL):	6.732
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.793
Skin Sensitization:	0.268
Carcinogencity:	0.404
Eye Corrosion:	0.074
Eye Irritation:	0.082
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC278628

Natural Product ID:	NPC278628
*Common Name:**	Rubiarbonone C
IUPAC Name:	[(1R,3S,3aR,5aS,5bS,6S,7aR,11aS,13aR,13bR)-1,6-dihydroxy-5a,8,8,11a,13a-pentamethyl-9-oxo-3-propan-2-yl-2,3,4,5,5b,6,7,7a,10,11,13,13b-dodecahydro-1H-cyclopenta[a]chrysen-3a-yl]methyl acetate
Synonyms:	Rubiarbonone C
Standard InCHIKey:	NKSVARYCVTXDAJ-DMDMSIRMSA-N
Standard InCHI:	InChI=1S/C32H50O5/c1-18(2)21-15-23(35)27-31(8)12-9-20-26(30(31,7)13-14-32(21,27)17-37-19(3)33)22(34)16-24-28(4,5)25(36)10-11-29(20,24)6/h9,18,21-24,26-27,34-35H,10-17H2,1-8H3/t21-,22-,23+,24-,26-,27+,29+,30-,31+,32+/m0/s1
SMILES:	CC(=O)OC[C@]12CC[C@@]3([C@]([C@H]2[C@@H](C[C@H]1C(C)C)O)(C)CC=C1[C@H]3[C@@H](O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468043
PubChem CID:	44566786
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	=	-2.3	%	PMID[537314]
NPT2	Others	Unspecified	Inhibition	=	3.7	%	PMID[537314]
NPT2	Others	Unspecified	Inhibition	=	-2.1	%	PMID[537314]
NPT2	Others	Unspecified	Inhibition	=	8.0	%	PMID[537314]
NPT2	Others	Unspecified	Inhibition	=	90.3	%	PMID[537314]

☑ 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 NPC278628 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	211
0.1-0.2	1353
0.2-0.3	4585
0.3-0.4	9960
0.4-0.5	11387
0.5-0.6	5638
0.6-0.7	4741
0.7-0.8	4229
0.8-0.85	518
0.85-0.9	62
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231530
0.9798	High Similarity	NPC94529
0.9412	High Similarity	NPC197428
0.9278	High Similarity	NPC190554
0.9208	High Similarity	NPC475571
0.92	High Similarity	NPC140723
0.9175	High Similarity	NPC253115
0.9175	High Similarity	NPC304899
0.9109	High Similarity	NPC29705
0.9091	High Similarity	NPC15390
0.899	High Similarity	NPC477854
0.899	High Similarity	NPC260149
0.899	High Similarity	NPC58942
0.898	High Similarity	NPC42042
0.898	High Similarity	NPC173272
0.8962	High Similarity	NPC202889
0.8911	High Similarity	NPC22388
0.89	High Similarity	NPC218383
0.89	High Similarity	NPC83709
0.89	High Similarity	NPC208358
0.8878	High Similarity	NPC469599
0.8878	High Similarity	NPC279974
0.8878	High Similarity	NPC48330
0.8868	High Similarity	NPC280782
0.8868	High Similarity	NPC71348
0.8835	High Similarity	NPC196528
0.8812	High Similarity	NPC155974
0.88	High Similarity	NPC119036
0.8796	High Similarity	NPC270958
0.8788	High Similarity	NPC477853
0.8785	High Similarity	NPC52634
0.8738	High Similarity	NPC96268
0.8687	High Similarity	NPC184848
0.8687	High Similarity	NPC69548
0.8687	High Similarity	NPC474727
0.8687	High Similarity	NPC473240
0.8673	High Similarity	NPC470376
0.8673	High Similarity	NPC473678
0.8673	High Similarity	NPC470375
0.8673	High Similarity	NPC206810
0.866	High Similarity	NPC471896
0.8641	High Similarity	NPC159442
0.8636	High Similarity	NPC118638
0.8627	High Similarity	NPC253886
0.8627	High Similarity	NPC474327
0.8627	High Similarity	NPC121218
0.8614	High Similarity	NPC477813
0.8614	High Similarity	NPC475876
0.8614	High Similarity	NPC114274
0.8611	High Similarity	NPC194100
0.8611	High Similarity	NPC962
0.86	High Similarity	NPC200054
0.86	High Similarity	NPC476327
0.86	High Similarity	NPC29410
0.86	High Similarity	NPC476318
0.8598	High Similarity	NPC231589
0.8598	High Similarity	NPC118860
0.8598	High Similarity	NPC214797
0.8586	High Similarity	NPC111015
0.8585	High Similarity	NPC241927
0.8585	High Similarity	NPC258543
0.8571	High Similarity	NPC154101
0.8571	High Similarity	NPC59530
0.8571	High Similarity	NPC26888
0.8559	High Similarity	NPC475041
0.8558	High Similarity	NPC477812
0.8544	High Similarity	NPC473928
0.8544	High Similarity	NPC136289
0.8544	High Similarity	NPC193934
0.8544	High Similarity	NPC170615
0.8544	High Similarity	NPC271980
0.8529	High Similarity	NPC167974
0.8519	High Similarity	NPC170487
0.8515	High Similarity	NPC108078
0.8515	High Similarity	NPC475032
0.8515	High Similarity	NPC476878
0.8515	High Similarity	NPC189880
0.8515	High Similarity	NPC476879
0.8515	High Similarity	NPC475033
0.85	High Similarity	NPC470016
0.85	High Similarity	NPC317586
0.85	High Similarity	NPC98639
0.8491	Intermediate Similarity	NPC275539
0.8491	Intermediate Similarity	NPC472217
0.8491	Intermediate Similarity	NPC472219
0.8491	Intermediate Similarity	NPC189075
0.8491	Intermediate Similarity	NPC469845
0.8491	Intermediate Similarity	NPC472218
0.8491	Intermediate Similarity	NPC211224
0.8485	Intermediate Similarity	NPC244356
0.8485	Intermediate Similarity	NPC224060
0.8485	Intermediate Similarity	NPC477855
0.8476	Intermediate Similarity	NPC181265
0.8476	Intermediate Similarity	NPC37600
0.8469	Intermediate Similarity	NPC175628
0.8469	Intermediate Similarity	NPC111585
0.8469	Intermediate Similarity	NPC148414
0.8462	Intermediate Similarity	NPC95585
0.8462	Intermediate Similarity	NPC469985
0.8462	Intermediate Similarity	NPC87927
0.8462	Intermediate Similarity	NPC282233
0.8462	Intermediate Similarity	NPC222153
0.8455	Intermediate Similarity	NPC266728
0.8455	Intermediate Similarity	NPC49492
0.8447	Intermediate Similarity	NPC289148
0.8447	Intermediate Similarity	NPC81530
0.8447	Intermediate Similarity	NPC163963
0.8447	Intermediate Similarity	NPC52899
0.844	Intermediate Similarity	NPC250109
0.8431	Intermediate Similarity	NPC153792
0.8431	Intermediate Similarity	NPC471038
0.8431	Intermediate Similarity	NPC271387
0.8431	Intermediate Similarity	NPC38471
0.8431	Intermediate Similarity	NPC20479
0.8431	Intermediate Similarity	NPC98837
0.8431	Intermediate Similarity	NPC38296
0.8431	Intermediate Similarity	NPC162459
0.8431	Intermediate Similarity	NPC28864
0.8426	Intermediate Similarity	NPC470281
0.8416	Intermediate Similarity	NPC329910
0.8416	Intermediate Similarity	NPC327179
0.8416	Intermediate Similarity	NPC475178
0.84	Intermediate Similarity	NPC159410
0.84	Intermediate Similarity	NPC166906
0.8396	Intermediate Similarity	NPC220974
0.8396	Intermediate Similarity	NPC110496
0.8396	Intermediate Similarity	NPC44063
0.8384	Intermediate Similarity	NPC77099
0.8384	Intermediate Similarity	NPC470590
0.8384	Intermediate Similarity	NPC285184
0.8384	Intermediate Similarity	NPC23434
0.8384	Intermediate Similarity	NPC60755
0.8381	Intermediate Similarity	NPC310586
0.8381	Intermediate Similarity	NPC475036
0.8381	Intermediate Similarity	NPC28656
0.8381	Intermediate Similarity	NPC47281
0.8381	Intermediate Similarity	NPC235889
0.8381	Intermediate Similarity	NPC149124
0.8381	Intermediate Similarity	NPC471293
0.8381	Intermediate Similarity	NPC75531
0.8367	Intermediate Similarity	NPC475921
0.8367	Intermediate Similarity	NPC474889
0.8367	Intermediate Similarity	NPC474704
0.8365	Intermediate Similarity	NPC473788
0.8365	Intermediate Similarity	NPC76866
0.8365	Intermediate Similarity	NPC286519
0.8365	Intermediate Similarity	NPC15396
0.8365	Intermediate Similarity	NPC475558
0.8365	Intermediate Similarity	NPC304832
0.8365	Intermediate Similarity	NPC214946
0.8365	Intermediate Similarity	NPC185530
0.8365	Intermediate Similarity	NPC477054
0.8365	Intermediate Similarity	NPC88203
0.8365	Intermediate Similarity	NPC148628
0.8365	Intermediate Similarity	NPC246736
0.8364	Intermediate Similarity	NPC243354
0.8351	Intermediate Similarity	NPC142361
0.8351	Intermediate Similarity	NPC474684
0.835	Intermediate Similarity	NPC94906
0.835	Intermediate Similarity	NPC287676
0.835	Intermediate Similarity	NPC108371
0.835	Intermediate Similarity	NPC293866
0.8349	Intermediate Similarity	NPC152117
0.8349	Intermediate Similarity	NPC234042
0.8333	Intermediate Similarity	NPC6206
0.8333	Intermediate Similarity	NPC65858
0.8333	Intermediate Similarity	NPC163314
0.8333	Intermediate Similarity	NPC269642
0.8319	Intermediate Similarity	NPC471406
0.8318	Intermediate Similarity	NPC295389
0.8318	Intermediate Similarity	NPC258323
0.8317	Intermediate Similarity	NPC470232
0.8317	Intermediate Similarity	NPC222845
0.8317	Intermediate Similarity	NPC45324
0.8317	Intermediate Similarity	NPC139570
0.8317	Intermediate Similarity	NPC472485
0.8317	Intermediate Similarity	NPC470229
0.8317	Intermediate Similarity	NPC162001
0.8302	Intermediate Similarity	NPC50535
0.8302	Intermediate Similarity	NPC102352
0.8302	Intermediate Similarity	NPC295366
0.8302	Intermediate Similarity	NPC265127
0.8302	Intermediate Similarity	NPC28791
0.83	Intermediate Similarity	NPC170220
0.83	Intermediate Similarity	NPC86368
0.83	Intermediate Similarity	NPC470224
0.83	Intermediate Similarity	NPC141497
0.83	Intermediate Similarity	NPC107674
0.8288	Intermediate Similarity	NPC190286
0.8288	Intermediate Similarity	NPC298278
0.8286	Intermediate Similarity	NPC90177
0.8286	Intermediate Similarity	NPC236390
0.8286	Intermediate Similarity	NPC55872
0.8286	Intermediate Similarity	NPC312900
0.8286	Intermediate Similarity	NPC26478
0.8286	Intermediate Similarity	NPC36688
0.8286	Intermediate Similarity	NPC191892
0.8286	Intermediate Similarity	NPC470310
0.8286	Intermediate Similarity	NPC95899
0.8286	Intermediate Similarity	NPC275583

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 NPC278628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1591
0.2-0.3	3912
0.3-0.4	2285
0.4-0.5	644
0.5-0.6	196
0.6-0.7	153
0.7-0.8	153
0.8-0.85	37
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD7128	Approved
0.8654	High Similarity	NPD6402	Approved
0.8654	High Similarity	NPD5739	Approved
0.8654	High Similarity	NPD6675	Approved
0.8491	Intermediate Similarity	NPD7320	Approved
0.8491	Intermediate Similarity	NPD6881	Approved
0.8491	Intermediate Similarity	NPD6899	Approved
0.8485	Intermediate Similarity	NPD6399	Phase 3
0.8476	Intermediate Similarity	NPD6008	Approved
0.8426	Intermediate Similarity	NPD8130	Phase 1
0.8411	Intermediate Similarity	NPD6373	Approved
0.8411	Intermediate Similarity	NPD6372	Approved
0.8396	Intermediate Similarity	NPD5697	Approved
0.8396	Intermediate Similarity	NPD5701	Approved
0.8349	Intermediate Similarity	NPD8297	Approved
0.8333	Intermediate Similarity	NPD7290	Approved
0.8333	Intermediate Similarity	NPD6883	Approved
0.8333	Intermediate Similarity	NPD7102	Approved
0.8318	Intermediate Similarity	NPD6011	Approved
0.8273	Intermediate Similarity	NPD4632	Approved
0.8257	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8257	Intermediate Similarity	NPD6617	Approved
0.8257	Intermediate Similarity	NPD6869	Approved
0.8257	Intermediate Similarity	NPD6649	Approved
0.8257	Intermediate Similarity	NPD6650	Approved
0.8257	Intermediate Similarity	NPD6847	Approved
0.8252	Intermediate Similarity	NPD7638	Approved
0.8241	Intermediate Similarity	NPD6014	Approved
0.8241	Intermediate Similarity	NPD6013	Approved
0.8241	Intermediate Similarity	NPD6012	Approved
0.8218	Intermediate Similarity	NPD7748	Approved
0.82	Intermediate Similarity	NPD8035	Phase 2
0.82	Intermediate Similarity	NPD8034	Phase 2
0.8182	Intermediate Similarity	NPD5328	Approved
0.8182	Intermediate Similarity	NPD6882	Approved
0.8173	Intermediate Similarity	NPD7640	Approved
0.8173	Intermediate Similarity	NPD7639	Approved
0.8155	Intermediate Similarity	NPD7902	Approved
0.8155	Intermediate Similarity	NPD4755	Approved
0.8136	Intermediate Similarity	NPD7736	Approved
0.8081	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD6009	Approved
0.8041	Intermediate Similarity	NPD4786	Approved
0.802	Intermediate Similarity	NPD6079	Approved
0.802	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD6319	Approved
0.8	Intermediate Similarity	NPD4700	Approved
0.8	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD5285	Approved
0.7981	Intermediate Similarity	NPD6083	Phase 2
0.7981	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7604	Phase 2
0.7941	Intermediate Similarity	NPD4202	Approved
0.7931	Intermediate Similarity	NPD5983	Phase 2
0.7925	Intermediate Similarity	NPD5223	Approved
0.7899	Intermediate Similarity	NPD8293	Discontinued
0.789	Intermediate Similarity	NPD6412	Phase 2
0.7881	Intermediate Similarity	NPD7492	Approved
0.7879	Intermediate Similarity	NPD7521	Approved
0.7879	Intermediate Similarity	NPD7334	Approved
0.7879	Intermediate Similarity	NPD6409	Approved
0.7879	Intermediate Similarity	NPD7146	Approved
0.7879	Intermediate Similarity	NPD5330	Approved
0.7879	Intermediate Similarity	NPD6684	Approved
0.7864	Intermediate Similarity	NPD7900	Approved
0.7864	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD5225	Approved
0.785	Intermediate Similarity	NPD5226	Approved
0.785	Intermediate Similarity	NPD5224	Approved
0.785	Intermediate Similarity	NPD5211	Phase 2
0.785	Intermediate Similarity	NPD4633	Approved
0.7845	Intermediate Similarity	NPD6054	Approved
0.7845	Intermediate Similarity	NPD6059	Approved
0.7835	Intermediate Similarity	NPD3667	Approved
0.7826	Intermediate Similarity	NPD6335	Approved
0.7815	Intermediate Similarity	NPD6616	Approved
0.7815	Intermediate Similarity	NPD6336	Discontinued
0.7815	Intermediate Similarity	NPD7507	Approved
0.7807	Intermediate Similarity	NPD6274	Approved
0.7778	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD4754	Approved
0.7778	Intermediate Similarity	NPD5175	Approved
0.7759	Intermediate Similarity	NPD7100	Approved
0.7759	Intermediate Similarity	NPD7101	Approved
0.775	Intermediate Similarity	NPD7078	Approved
0.7739	Intermediate Similarity	NPD6317	Approved
0.7723	Intermediate Similarity	NPD6903	Approved
0.7714	Intermediate Similarity	NPD5222	Approved
0.7714	Intermediate Similarity	NPD5221	Approved
0.7714	Intermediate Similarity	NPD4697	Phase 3
0.7714	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6370	Approved
0.7706	Intermediate Similarity	NPD5141	Approved
0.77	Intermediate Similarity	NPD3618	Phase 1
0.7679	Intermediate Similarity	NPD4634	Approved
0.7677	Intermediate Similarity	NPD3665	Phase 1
0.7677	Intermediate Similarity	NPD3133	Approved
0.7677	Intermediate Similarity	NPD3666	Approved
0.7672	Intermediate Similarity	NPD6314	Approved
0.7672	Intermediate Similarity	NPD6313	Approved
0.7642	Intermediate Similarity	NPD5173	Approved
0.7636	Intermediate Similarity	NPD4767	Approved
0.7636	Intermediate Similarity	NPD4768	Approved
0.7627	Intermediate Similarity	NPD6016	Approved
0.7627	Intermediate Similarity	NPD6909	Approved
0.7627	Intermediate Similarity	NPD6908	Approved
0.7627	Intermediate Similarity	NPD6015	Approved
0.7623	Intermediate Similarity	NPD7319	Approved
0.7619	Intermediate Similarity	NPD5695	Phase 3
0.7619	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5696	Approved
0.7563	Intermediate Similarity	NPD5988	Approved
0.7549	Intermediate Similarity	NPD5737	Approved
0.7549	Intermediate Similarity	NPD6672	Approved
0.7544	Intermediate Similarity	NPD6053	Discontinued
0.7525	Intermediate Similarity	NPD6098	Approved
0.7523	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD4730	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD5128	Approved
0.75	Intermediate Similarity	NPD4729	Approved
0.7479	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6080	Approved
0.7476	Intermediate Similarity	NPD6673	Approved
0.7476	Intermediate Similarity	NPD4753	Phase 2
0.7476	Intermediate Similarity	NPD6904	Approved
0.7449	Intermediate Similarity	NPD7525	Registered
0.7436	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7115	Discovery
0.7434	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6697	Approved
0.7423	Intermediate Similarity	NPD6118	Approved
0.7423	Intermediate Similarity	NPD6114	Approved
0.7423	Intermediate Similarity	NPD6115	Approved
0.7398	Intermediate Similarity	NPD6033	Approved
0.7368	Intermediate Similarity	NPD5169	Approved
0.7368	Intermediate Similarity	NPD5247	Approved
0.7368	Intermediate Similarity	NPD5249	Phase 3
0.7368	Intermediate Similarity	NPD5135	Approved
0.7368	Intermediate Similarity	NPD5251	Approved
0.7368	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5250	Approved
0.7368	Intermediate Similarity	NPD5248	Approved
0.7333	Intermediate Similarity	NPD5284	Approved
0.7333	Intermediate Similarity	NPD8033	Approved
0.7333	Intermediate Similarity	NPD6411	Approved
0.7333	Intermediate Similarity	NPD5281	Approved
0.7328	Intermediate Similarity	NPD8133	Approved
0.7327	Intermediate Similarity	NPD3668	Phase 3
0.732	Intermediate Similarity	NPD6116	Phase 1
0.7304	Intermediate Similarity	NPD5216	Approved
0.7304	Intermediate Similarity	NPD5217	Approved
0.7304	Intermediate Similarity	NPD5215	Approved
0.7304	Intermediate Similarity	NPD5127	Approved
0.73	Intermediate Similarity	NPD4221	Approved
0.73	Intermediate Similarity	NPD4223	Phase 3
0.73	Intermediate Similarity	NPD6435	Approved
0.7282	Intermediate Similarity	NPD3573	Approved
0.7255	Intermediate Similarity	NPD5329	Approved
0.725	Intermediate Similarity	NPD8377	Approved
0.725	Intermediate Similarity	NPD8294	Approved
0.7228	Intermediate Similarity	NPD4788	Approved
0.7227	Intermediate Similarity	NPD7327	Approved
0.7227	Intermediate Similarity	NPD7328	Approved
0.7216	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6117	Approved
0.7213	Intermediate Similarity	NPD6067	Discontinued
0.7212	Intermediate Similarity	NPD5208	Approved
0.7196	Intermediate Similarity	NPD6001	Approved
0.719	Intermediate Similarity	NPD8380	Approved
0.719	Intermediate Similarity	NPD8379	Approved
0.719	Intermediate Similarity	NPD8335	Approved
0.719	Intermediate Similarity	NPD8378	Approved
0.719	Intermediate Similarity	NPD8296	Approved
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5693	Phase 1
0.7167	Intermediate Similarity	NPD7516	Approved
0.7157	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4629	Approved
0.713	Intermediate Similarity	NPD5210	Approved
0.7119	Intermediate Similarity	NPD5167	Approved
0.7113	Intermediate Similarity	NPD7339	Approved
0.7113	Intermediate Similarity	NPD3703	Phase 2
0.7113	Intermediate Similarity	NPD6942	Approved
0.7103	Intermediate Similarity	NPD5778	Approved
0.7103	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5368	Approved
0.708	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7043	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5168	Approved
0.7023	Intermediate Similarity	NPD6333	Approved
0.7023	Intermediate Similarity	NPD6334	Approved
0.7019	Intermediate Similarity	NPD4138	Approved
0.7019	Intermediate Similarity	NPD5279	Phase 3

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