NPASS Compound

Structure

NPC15390 OpenBabel07101719122D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 0 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 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 -1.8171 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5352 -2.5181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 16 1 0 0 0 0 2 16 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 9 1 0 0 0 0 8 17 2 0 0 0 0 9 29 1 0 0 0 0 10 11 1 0 0 0 0 10 28 1 0 0 0 0 11 30 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 27 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 6 0 0 0 19 23 1 0 0 0 0 19 32 1 6 0 0 0 20 24 1 0 0 0 0 20 33 1 1 0 0 0 21 25 1 0 0 0 0 21 34 1 1 0 0 0 22 26 1 0 0 0 0 22 27 1 6 0 0 0 23 28 1 1 0 0 0 24 29 1 6 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 35 2 0 0 0 0 27 5 1 6 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	523.332
LogP:	4.01
LogD:	3.854
LogS:	-4.193
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	5.508
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:	-5.098
MDCK Permeability:	5.230561328062322e-06
Pgp-inhibitor:	0.081
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.795
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.642
Plasma Protein Binding (PPB):	76.16007995605469%
Volume Distribution (VD):	0.763
Pgp-substrate:	14.918608665466309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	6.711
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.694
Skin Sensitization:	0.223
Carcinogencity:	0.084
Eye Corrosion:	0.129
Eye Irritation:	0.033
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: NPC15390

Natural Product ID:	NPC15390
*Common Name:**	2Alpha,7Beta,19Alpha,28-Tetrahydroxy-9(11)-Arborinen-3-One
IUPAC Name:	(1R,3S,3aR,5aS,5bS,6S,7aR,10R,11aS,13aR,13bR)-1,6,10-trihydroxy-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:	rubianol-a
Standard InCHIKey:	ZAGSMKWHSPITNU-AZAFKCFLSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-16(2)18-12-20(33)24-29(7)9-8-17-23(28(29,6)10-11-30(18,24)15-31)19(32)13-22-26(3,4)25(35)21(34)14-27(17,22)5/h8,16,18-24,31-34H,9-15H2,1-7H3/t18-,19-,20+,21+,22-,23-,24+,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)[C@@H](C[C@]45C)O)O)[C@]3(C)CC[C@@]12CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467417
PubChem CID:	21629620
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	=	1.8	%	PMID[572600]
NPT2	Others	Unspecified	Inhibition	=	2.1	%	PMID[572600]
NPT2	Others	Unspecified	Inhibition	=	-10.3	%	PMID[572600]
NPT2	Others	Unspecified	Inhibition	=	-9.6	%	PMID[572600]
NPT2	Others	Unspecified	Inhibition	=	40.3	%	PMID[572600]

☑ 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 NPC15390 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	201
0.1-0.2	1393
0.2-0.3	5134
0.3-0.4	12399
0.4-0.5	9703
0.5-0.6	5695
0.6-0.7	5088
0.7-0.8	2718
0.8-0.85	315
0.85-0.9	45
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC190554
0.9293	High Similarity	NPC94529
0.9091	High Similarity	NPC231530
0.9091	High Similarity	NPC278628
0.9082	High Similarity	NPC191892
0.9053	High Similarity	NPC49371
0.9043	High Similarity	NPC245972
0.9043	High Similarity	NPC196485
0.9043	High Similarity	NPC111015
0.8969	High Similarity	NPC83709
0.8958	High Similarity	NPC18509
0.8854	High Similarity	NPC173272
0.883	High Similarity	NPC168027
0.883	High Similarity	NPC185936
0.8817	High Similarity	NPC76879
0.8817	High Similarity	NPC474245
0.8812	High Similarity	NPC165873
0.88	High Similarity	NPC29705
0.8776	High Similarity	NPC144956
0.875	High Similarity	NPC472485
0.875	High Similarity	NPC48330
0.8713	High Similarity	NPC475571
0.871	High Similarity	NPC193360
0.87	High Similarity	NPC117185
0.8696	High Similarity	NPC51014
0.8696	High Similarity	NPC24277
0.8696	High Similarity	NPC20688
0.8673	High Similarity	NPC477854
0.866	High Similarity	NPC477853
0.8627	High Similarity	NPC475060
0.8627	High Similarity	NPC220229
0.8617	High Similarity	NPC186688
0.8614	High Similarity	NPC137657
0.8586	High Similarity	NPC154072
0.8586	High Similarity	NPC110149
0.8571	High Similarity	NPC71348
0.8558	High Similarity	NPC197428
0.8557	High Similarity	NPC127063
0.8557	High Similarity	NPC473240
0.8544	High Similarity	NPC217201
0.8542	High Similarity	NPC206810
0.8542	High Similarity	NPC12722
0.8542	High Similarity	NPC470375
0.8542	High Similarity	NPC470376
0.8529	High Similarity	NPC214264
0.8529	High Similarity	NPC149047
0.8529	High Similarity	NPC171137
0.8529	High Similarity	NPC152695
0.8529	High Similarity	NPC97202
0.8529	High Similarity	NPC85829
0.8529	High Similarity	NPC48733
0.8529	High Similarity	NPC50692
0.8529	High Similarity	NPC260268
0.8529	High Similarity	NPC319077
0.8529	High Similarity	NPC476027
0.8529	High Similarity	NPC49958
0.8529	High Similarity	NPC296945
0.8529	High Similarity	NPC257353
0.8529	High Similarity	NPC302607
0.8529	High Similarity	NPC202167
0.8529	High Similarity	NPC150531
0.8526	High Similarity	NPC100313
0.8515	High Similarity	NPC140723
0.8511	High Similarity	NPC53911
0.8511	High Similarity	NPC328539
0.8511	High Similarity	NPC328313
0.8491	Intermediate Similarity	NPC73300
0.8491	Intermediate Similarity	NPC202889
0.8491	Intermediate Similarity	NPC108721
0.8485	Intermediate Similarity	NPC191565
0.8485	Intermediate Similarity	NPC114274
0.8478	Intermediate Similarity	NPC124172
0.8478	Intermediate Similarity	NPC209802
0.8478	Intermediate Similarity	NPC221758
0.8478	Intermediate Similarity	NPC82902
0.8478	Intermediate Similarity	NPC59453
0.8469	Intermediate Similarity	NPC476327
0.8469	Intermediate Similarity	NPC192428
0.8469	Intermediate Similarity	NPC96859
0.8469	Intermediate Similarity	NPC328162
0.8469	Intermediate Similarity	NPC476318
0.8469	Intermediate Similarity	NPC305483
0.8462	Intermediate Similarity	NPC11710
0.8454	Intermediate Similarity	NPC471207
0.8454	Intermediate Similarity	NPC280804
0.8447	Intermediate Similarity	NPC83744
0.8438	Intermediate Similarity	NPC272746
0.8431	Intermediate Similarity	NPC477812
0.8431	Intermediate Similarity	NPC149124
0.8431	Intermediate Similarity	NPC204833
0.8431	Intermediate Similarity	NPC209502
0.8431	Intermediate Similarity	NPC75531
0.8421	Intermediate Similarity	NPC477943
0.8421	Intermediate Similarity	NPC1015
0.8421	Intermediate Similarity	NPC31985
0.8421	Intermediate Similarity	NPC275740
0.8421	Intermediate Similarity	NPC86319
0.8421	Intermediate Similarity	NPC32830
0.8421	Intermediate Similarity	NPC122116
0.8421	Intermediate Similarity	NPC105495
0.8416	Intermediate Similarity	NPC271980
0.8416	Intermediate Similarity	NPC185530
0.8416	Intermediate Similarity	NPC193934
0.8404	Intermediate Similarity	NPC475740
0.8404	Intermediate Similarity	NPC317590
0.84	Intermediate Similarity	NPC218383
0.84	Intermediate Similarity	NPC474720
0.8396	Intermediate Similarity	NPC280782
0.8387	Intermediate Similarity	NPC474218
0.8384	Intermediate Similarity	NPC108078
0.8384	Intermediate Similarity	NPC189880
0.8381	Intermediate Similarity	NPC235077
0.8381	Intermediate Similarity	NPC163314
0.837	Intermediate Similarity	NPC476082
0.837	Intermediate Similarity	NPC110778
0.837	Intermediate Similarity	NPC278648
0.8367	Intermediate Similarity	NPC469599
0.8365	Intermediate Similarity	NPC329417
0.8351	Intermediate Similarity	NPC244356
0.8351	Intermediate Similarity	NPC224060
0.8351	Intermediate Similarity	NPC477855
0.8351	Intermediate Similarity	NPC475255
0.835	Intermediate Similarity	NPC196528
0.835	Intermediate Similarity	NPC166607
0.8333	Intermediate Similarity	NPC311612
0.8333	Intermediate Similarity	NPC249187
0.8333	Intermediate Similarity	NPC247957
0.8333	Intermediate Similarity	NPC171441
0.8333	Intermediate Similarity	NPC46758
0.8333	Intermediate Similarity	NPC85173
0.8333	Intermediate Similarity	NPC26478
0.8333	Intermediate Similarity	NPC270958
0.8318	Intermediate Similarity	NPC194100
0.8317	Intermediate Similarity	NPC118964
0.8316	Intermediate Similarity	NPC471722
0.8316	Intermediate Similarity	NPC143767
0.8316	Intermediate Similarity	NPC470542
0.8316	Intermediate Similarity	NPC131470
0.83	Intermediate Similarity	NPC260149
0.83	Intermediate Similarity	NPC58942
0.8298	Intermediate Similarity	NPC469994
0.8298	Intermediate Similarity	NPC327115
0.8298	Intermediate Similarity	NPC145879
0.8298	Intermediate Similarity	NPC31564
0.8298	Intermediate Similarity	NPC474732
0.8298	Intermediate Similarity	NPC474733
0.8298	Intermediate Similarity	NPC474778
0.8286	Intermediate Similarity	NPC214644
0.8286	Intermediate Similarity	NPC241927
0.8286	Intermediate Similarity	NPC258543
0.8283	Intermediate Similarity	NPC5532
0.8283	Intermediate Similarity	NPC469545
0.8283	Intermediate Similarity	NPC157113
0.8283	Intermediate Similarity	NPC61369
0.8283	Intermediate Similarity	NPC304899
0.8283	Intermediate Similarity	NPC253115
0.8283	Intermediate Similarity	NPC62516
0.828	Intermediate Similarity	NPC475798
0.828	Intermediate Similarity	NPC127606
0.828	Intermediate Similarity	NPC474233
0.8269	Intermediate Similarity	NPC477916
0.8269	Intermediate Similarity	NPC44063
0.8269	Intermediate Similarity	NPC185
0.8269	Intermediate Similarity	NPC472925
0.8269	Intermediate Similarity	NPC144459
0.8265	Intermediate Similarity	NPC302008
0.8265	Intermediate Similarity	NPC209662
0.8265	Intermediate Similarity	NPC23170
0.8265	Intermediate Similarity	NPC191094
0.8265	Intermediate Similarity	NPC166906
0.8261	Intermediate Similarity	NPC1272
0.8261	Intermediate Similarity	NPC48362
0.8261	Intermediate Similarity	NPC151519
0.8261	Intermediate Similarity	NPC470614
0.8252	Intermediate Similarity	NPC72255
0.8252	Intermediate Similarity	NPC235889
0.8252	Intermediate Similarity	NPC160843
0.8247	Intermediate Similarity	NPC474525
0.8247	Intermediate Similarity	NPC154101
0.8247	Intermediate Similarity	NPC23434
0.8247	Intermediate Similarity	NPC476168
0.8235	Intermediate Similarity	NPC477054
0.8235	Intermediate Similarity	NPC87351
0.8235	Intermediate Similarity	NPC477915
0.8235	Intermediate Similarity	NPC22388
0.8235	Intermediate Similarity	NPC473424
0.8229	Intermediate Similarity	NPC474704
0.8229	Intermediate Similarity	NPC326627
0.8229	Intermediate Similarity	NPC69627
0.8229	Intermediate Similarity	NPC310010
0.8229	Intermediate Similarity	NPC475921
0.8218	Intermediate Similarity	NPC327431
0.8211	Intermediate Similarity	NPC472495
0.8211	Intermediate Similarity	NPC298904
0.8211	Intermediate Similarity	NPC153604
0.8211	Intermediate Similarity	NPC4643
0.8211	Intermediate Similarity	NPC57469
0.8211	Intermediate Similarity	NPC474684
0.8211	Intermediate Similarity	NPC73064
0.8211	Intermediate Similarity	NPC58063

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 NPC15390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1648
0.2-0.3	4110
0.3-0.4	2180
0.4-0.5	549
0.5-0.6	169
0.6-0.7	137
0.7-0.8	118
0.8-0.85	57
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8958	High Similarity	NPD4755	Approved
0.8776	High Similarity	NPD5285	Approved
0.8776	High Similarity	NPD4700	Approved
0.8776	High Similarity	NPD4696	Approved
0.8776	High Similarity	NPD5286	Approved
0.8687	High Similarity	NPD5223	Approved
0.8617	High Similarity	NPD5328	Approved
0.86	High Similarity	NPD4633	Approved
0.86	High Similarity	NPD5225	Approved
0.86	High Similarity	NPD5224	Approved
0.86	High Similarity	NPD5226	Approved
0.86	High Similarity	NPD5211	Phase 2
0.8529	High Similarity	NPD5739	Approved
0.8529	High Similarity	NPD7128	Approved
0.8529	High Similarity	NPD6675	Approved
0.8529	High Similarity	NPD6402	Approved
0.8515	High Similarity	NPD5174	Approved
0.8515	High Similarity	NPD5175	Approved
0.8515	High Similarity	NPD4754	Approved
0.8478	Intermediate Similarity	NPD4786	Approved
0.8469	Intermediate Similarity	NPD5222	Approved
0.8469	Intermediate Similarity	NPD5221	Approved
0.8469	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8469	Intermediate Similarity	NPD4697	Phase 3
0.8438	Intermediate Similarity	NPD6079	Approved
0.8431	Intermediate Similarity	NPD5141	Approved
0.8384	Intermediate Similarity	NPD5173	Approved
0.8381	Intermediate Similarity	NPD4634	Approved
0.8365	Intermediate Similarity	NPD6899	Approved
0.8365	Intermediate Similarity	NPD6881	Approved
0.8365	Intermediate Similarity	NPD7320	Approved
0.8351	Intermediate Similarity	NPD4202	Approved
0.835	Intermediate Similarity	NPD4768	Approved
0.835	Intermediate Similarity	NPD4767	Approved
0.8286	Intermediate Similarity	NPD6372	Approved
0.8286	Intermediate Similarity	NPD6373	Approved
0.8269	Intermediate Similarity	NPD5701	Approved
0.8269	Intermediate Similarity	NPD5697	Approved
0.8261	Intermediate Similarity	NPD3667	Approved
0.8229	Intermediate Similarity	NPD4753	Phase 2
0.8208	Intermediate Similarity	NPD6883	Approved
0.8208	Intermediate Similarity	NPD7290	Approved
0.8208	Intermediate Similarity	NPD7102	Approved
0.819	Intermediate Similarity	NPD4730	Approved
0.819	Intermediate Similarity	NPD4729	Approved
0.819	Intermediate Similarity	NPD6011	Approved
0.819	Intermediate Similarity	NPD5128	Approved
0.8148	Intermediate Similarity	NPD4632	Approved
0.8131	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD6869	Approved
0.8131	Intermediate Similarity	NPD8130	Phase 1
0.8131	Intermediate Similarity	NPD6649	Approved
0.8131	Intermediate Similarity	NPD6847	Approved
0.8131	Intermediate Similarity	NPD6617	Approved
0.8131	Intermediate Similarity	NPD6650	Approved
0.8113	Intermediate Similarity	NPD6013	Approved
0.8113	Intermediate Similarity	NPD6012	Approved
0.8113	Intermediate Similarity	NPD6014	Approved
0.8105	Intermediate Similarity	NPD3618	Phase 1
0.8085	Intermediate Similarity	NPD3666	Approved
0.8085	Intermediate Similarity	NPD3665	Phase 1
0.8085	Intermediate Similarity	NPD3133	Approved
0.8056	Intermediate Similarity	NPD8297	Approved
0.8056	Intermediate Similarity	NPD6882	Approved
0.8037	Intermediate Similarity	NPD5247	Approved
0.8037	Intermediate Similarity	NPD5135	Approved
0.8037	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5169	Approved
0.8037	Intermediate Similarity	NPD5251	Approved
0.8037	Intermediate Similarity	NPD5249	Phase 3
0.8037	Intermediate Similarity	NPD5248	Approved
0.8037	Intermediate Similarity	NPD5250	Approved
0.8	Intermediate Similarity	NPD5329	Approved
0.798	Intermediate Similarity	NPD6399	Phase 3
0.7963	Intermediate Similarity	NPD5216	Approved
0.7963	Intermediate Similarity	NPD5127	Approved
0.7963	Intermediate Similarity	NPD5215	Approved
0.7963	Intermediate Similarity	NPD5217	Approved
0.7928	Intermediate Similarity	NPD6009	Approved
0.7895	Intermediate Similarity	NPD4197	Approved
0.7879	Intermediate Similarity	NPD7515	Phase 2
0.7876	Intermediate Similarity	NPD6059	Approved
0.7876	Intermediate Similarity	NPD6054	Approved
0.7849	Intermediate Similarity	NPD7525	Registered
0.7843	Intermediate Similarity	NPD6083	Phase 2
0.7843	Intermediate Similarity	NPD6084	Phase 2
0.783	Intermediate Similarity	NPD6008	Approved
0.7822	Intermediate Similarity	NPD5210	Approved
0.7822	Intermediate Similarity	NPD4629	Approved
0.7812	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5167	Approved
0.7739	Intermediate Similarity	NPD6370	Approved
0.7732	Intermediate Similarity	NPD5279	Phase 3
0.7719	Intermediate Similarity	NPD6319	Approved
0.7712	Intermediate Similarity	NPD7736	Approved
0.7708	Intermediate Similarity	NPD3668	Phase 3
0.7699	Intermediate Similarity	NPD6335	Approved
0.7685	Intermediate Similarity	NPD5168	Approved
0.7684	Intermediate Similarity	NPD4221	Approved
0.7684	Intermediate Similarity	NPD4223	Phase 3
0.7679	Intermediate Similarity	NPD6274	Approved
0.7672	Intermediate Similarity	NPD7604	Phase 2
0.7652	Intermediate Similarity	NPD5983	Phase 2
0.7652	Intermediate Similarity	NPD6016	Approved
0.7652	Intermediate Similarity	NPD6015	Approved
0.7632	Intermediate Similarity	NPD7101	Approved
0.7632	Intermediate Similarity	NPD7100	Approved
0.7611	Intermediate Similarity	NPD6317	Approved
0.7609	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7492	Approved
0.7604	Intermediate Similarity	NPD4788	Approved
0.7596	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD6412	Phase 2
0.7586	Intermediate Similarity	NPD5988	Approved
0.7576	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5690	Phase 2
0.7551	Intermediate Similarity	NPD5280	Approved
0.7551	Intermediate Similarity	NPD4694	Approved
0.7549	Intermediate Similarity	NPD7748	Approved
0.7544	Intermediate Similarity	NPD6314	Approved
0.7544	Intermediate Similarity	NPD6313	Approved
0.7542	Intermediate Similarity	NPD6616	Approved
0.7542	Intermediate Similarity	NPD6336	Discontinued
0.7525	Intermediate Similarity	NPD8034	Phase 2
0.7525	Intermediate Similarity	NPD8035	Phase 2
0.7524	Intermediate Similarity	NPD7640	Approved
0.7524	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD6909	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6908	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7479	Intermediate Similarity	NPD7078	Approved
0.7479	Intermediate Similarity	NPD8293	Discontinued
0.7476	Intermediate Similarity	NPD5695	Phase 3
0.7429	Intermediate Similarity	NPD5696	Approved
0.7417	Intermediate Similarity	NPD6033	Approved
0.74	Intermediate Similarity	NPD6672	Approved
0.74	Intermediate Similarity	NPD5737	Approved
0.7374	Intermediate Similarity	NPD4138	Approved
0.7374	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6098	Approved
0.7374	Intermediate Similarity	NPD6409	Approved
0.7374	Intermediate Similarity	NPD7146	Approved
0.7374	Intermediate Similarity	NPD5205	Approved
0.7374	Intermediate Similarity	NPD4690	Approved
0.7374	Intermediate Similarity	NPD4693	Phase 3
0.7374	Intermediate Similarity	NPD4688	Approved
0.7374	Intermediate Similarity	NPD6684	Approved
0.7374	Intermediate Similarity	NPD7521	Approved
0.7374	Intermediate Similarity	NPD7334	Approved
0.7374	Intermediate Similarity	NPD4689	Approved
0.7374	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD6868	Approved
0.735	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6673	Approved
0.7327	Intermediate Similarity	NPD6904	Approved
0.7327	Intermediate Similarity	NPD6080	Approved
0.73	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4695	Discontinued
0.7263	Intermediate Similarity	NPD6697	Approved
0.7263	Intermediate Similarity	NPD6118	Approved
0.7263	Intermediate Similarity	NPD3617	Approved
0.7263	Intermediate Similarity	NPD6115	Approved
0.7263	Intermediate Similarity	NPD6114	Approved
0.725	Intermediate Similarity	NPD7507	Approved
0.7228	Intermediate Similarity	NPD6903	Approved
0.7212	Intermediate Similarity	NPD7900	Approved
0.7212	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7645	Phase 2
0.7184	Intermediate Similarity	NPD5284	Approved
0.7184	Intermediate Similarity	NPD5281	Approved
0.7174	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6116	Phase 1
0.7157	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8328	Phase 3
0.7073	Intermediate Similarity	NPD7319	Approved
0.7065	Intermediate Similarity	NPD4245	Approved
0.7065	Intermediate Similarity	NPD4244	Approved
0.7065	Intermediate Similarity	NPD4789	Approved
0.7053	Intermediate Similarity	NPD6117	Approved
0.7041	Intermediate Similarity	NPD4692	Approved
0.7041	Intermediate Similarity	NPD4139	Approved
0.7034	Intermediate Similarity	NPD4522	Approved
0.7021	Intermediate Similarity	NPD4785	Approved
0.7021	Intermediate Similarity	NPD4784	Approved
0.7019	Intermediate Similarity	NPD5693	Phase 1
0.7019	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD4195	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7009	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4243	Approved
0.6957	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6053	Discontinued
0.6957	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3698	Phase 2
0.6952	Remote Similarity	NPD5133	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