NPASS Compound

Structure

NPC183270 OpenBabel07101719142D 40 44 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 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 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 -2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9538 -2.8479 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 0.3660 -2.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 28 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 18 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 16 23 1 0 0 0 0 16 31 1 0 0 0 0 17 31 1 0 0 0 0 17 36 1 0 0 0 0 18 29 1 0 0 0 0 19 32 2 0 0 0 0 19 37 1 0 0 0 0 20 33 2 0 0 0 0 20 38 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 39 1 1 0 0 0 23 34 2 0 0 0 0 23 36 1 0 0 0 0 24 28 1 6 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 6 0 0 0 25 37 1 0 0 0 0 26 30 1 1 0 0 0 26 38 1 0 0 0 0 27 35 2 0 0 0 0 27 39 1 0 0 0 0 28 30 1 6 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 30 40 1 0 0 0 0 31 15 1 6 0 0 0 31 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.25
Volume:	559.97
LogP:	3.697
LogD:	2.101
LogS:	-4.76
# Rotatable Bonds:	7
TPSA:	114.43
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	5.43
Fsp3:	0.613
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:	-5.261
MDCK Permeability:	4.846834417548962e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.578
Plasma Protein Binding (PPB):	83.88327026367188%
Volume Distribution (VD):	1.311
Pgp-substrate:	15.492792129516602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.218
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.258
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.885
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.434

ADMET: Excretion

Clearance (CL):	5.685
Half-life (T1/2):	0.659

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.677
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.618
Carcinogencity:	0.183
Eye Corrosion:	0.006
Eye Irritation:	0.176
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC183270

Natural Product ID:	NPC183270
*Common Name:**	Scutebata D
IUPAC Name:	[(3S,4aR,5S,6R,6aR,10R,10aS,10bR)-5,6-diacetyloxy-4a,6a,7,10b-tetramethyl-2'-oxospiro[2,5,6,9,10,10a-hexahydro-1H-benzo[f]chromene-3,4'-oxolane]-10-yl] benzoate
Synonyms:
Standard InCHIKey:	XYYMUFSAXSAILU-HQCFMCSESA-N
Standard InCHI:	InChI=1S/C31H38O9/c1-18-12-13-22(39-27(35)21-10-8-7-9-11-21)24-28(4)14-15-31(16-23(34)36-17-31)40-30(28,6)26(38-20(3)33)25(29(18,24)5)37-19(2)32/h7-12,22,24-26H,13-17H2,1-6H3/t22-,24-,25+,26+,28-,29+,30+,31+/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H](OC(=O)C)[C@]2(C)O[C@@]3(COC(=O)C3)CC[C@@]2([C@@H]2[C@]1(C)C(=CC[C@H]2OC(=O)c1ccccc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577082
PubChem CID:	46183387
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
EC50	1
Others	3

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	737700.0	nM	PMID[568332]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	12900.0	nM	PMID[568332]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	57.2	n.a.	PMID[568332]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	>	50.0	%	PMID[568332]

☑ 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 NPC183270 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	346
0.1-0.2	1191
0.2-0.3	2239
0.3-0.4	4570
0.4-0.5	9030
0.5-0.6	11834
0.6-0.7	11230
0.7-0.8	1802
0.8-0.85	216
0.85-0.9	92
0.9-0.95	145
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477904
0.9398	High Similarity	NPC66761
0.9398	High Similarity	NPC472577
0.9398	High Similarity	NPC17877
0.9398	High Similarity	NPC195647
0.9398	High Similarity	NPC291638
0.9323	High Similarity	NPC474608
0.9265	High Similarity	NPC473613
0.9265	High Similarity	NPC4341
0.9265	High Similarity	NPC473060
0.9265	High Similarity	NPC476094
0.9265	High Similarity	NPC43241
0.9265	High Similarity	NPC473758
0.9265	High Similarity	NPC473112
0.9265	High Similarity	NPC147880
0.9265	High Similarity	NPC211137
0.9265	High Similarity	NPC184747
0.9265	High Similarity	NPC48017
0.9265	High Similarity	NPC473109
0.9265	High Similarity	NPC200592
0.9265	High Similarity	NPC473081
0.9265	High Similarity	NPC473085
0.9259	High Similarity	NPC183122
0.9259	High Similarity	NPC283375
0.9225	High Similarity	NPC472548
0.9209	High Similarity	NPC471107
0.9209	High Similarity	NPC471100
0.9191	High Similarity	NPC210591
0.9191	High Similarity	NPC475652
0.9191	High Similarity	NPC214550
0.9167	High Similarity	NPC147561
0.9124	High Similarity	NPC97667
0.9124	High Similarity	NPC472547
0.9124	High Similarity	NPC171207
0.9124	High Similarity	NPC90614
0.9097	High Similarity	NPC472549
0.9091	High Similarity	NPC477905
0.9085	High Similarity	NPC254558
0.9065	High Similarity	NPC270498
0.9065	High Similarity	NPC163087
0.9065	High Similarity	NPC191082
0.9065	High Similarity	NPC473673
0.9065	High Similarity	NPC475429
0.9065	High Similarity	NPC147217
0.9065	High Similarity	NPC246480
0.9065	High Similarity	NPC139067
0.9065	High Similarity	NPC177340
0.9058	High Similarity	NPC118080
0.9058	High Similarity	NPC87448
0.9058	High Similarity	NPC41481
0.9058	High Similarity	NPC291599
0.9058	High Similarity	NPC27377
0.9058	High Similarity	NPC97947
0.9058	High Similarity	NPC472576
0.9058	High Similarity	NPC16912
0.9044	High Similarity	NPC472551
0.9044	High Similarity	NPC472545
0.9007	High Similarity	NPC474935
0.9	High Similarity	NPC57628
0.9	High Similarity	NPC95810
0.9	High Similarity	NPC241951
0.9	High Similarity	NPC470152
0.9	High Similarity	NPC11685
0.9	High Similarity	NPC67777
0.9	High Similarity	NPC472570
0.9	High Similarity	NPC163719
0.9	High Similarity	NPC51314
0.9	High Similarity	NPC472569
0.9	High Similarity	NPC476974
0.9	High Similarity	NPC475759
0.9	High Similarity	NPC70716
0.9	High Similarity	NPC125106
0.9	High Similarity	NPC470231
0.9	High Similarity	NPC25768
0.9	High Similarity	NPC472573
0.9	High Similarity	NPC95265
0.9	High Similarity	NPC188865
0.8986	High Similarity	NPC100913
0.8986	High Similarity	NPC275592
0.8978	High Similarity	NPC39549
0.8944	High Similarity	NPC217918
0.8936	High Similarity	NPC476973
0.8936	High Similarity	NPC174982
0.8936	High Similarity	NPC472571
0.8936	High Similarity	NPC184817
0.8936	High Similarity	NPC472572
0.8936	High Similarity	NPC200471
0.8936	High Similarity	NPC470159
0.8936	High Similarity	NPC127857
0.8936	High Similarity	NPC472575
0.8936	High Similarity	NPC29704
0.8936	High Similarity	NPC70403
0.8936	High Similarity	NPC96903
0.8936	High Similarity	NPC471104
0.8936	High Similarity	NPC470157
0.8936	High Similarity	NPC472568
0.8936	High Similarity	NPC469349
0.8936	High Similarity	NPC158663
0.8936	High Similarity	NPC177940
0.8936	High Similarity	NPC473088
0.8936	High Similarity	NPC171525
0.8921	High Similarity	NPC224491
0.8889	High Similarity	NPC306799
0.8889	High Similarity	NPC471103
0.8889	High Similarity	NPC472394
0.8889	High Similarity	NPC51602
0.8889	High Similarity	NPC470153
0.8889	High Similarity	NPC101043
0.8881	High Similarity	NPC60509
0.8881	High Similarity	NPC81698
0.8881	High Similarity	NPC250046
0.8865	High Similarity	NPC475122
0.8857	High Similarity	NPC34012
0.8857	High Similarity	NPC472546
0.8841	High Similarity	NPC475373
0.8836	High Similarity	NPC282239
0.8832	High Similarity	NPC473216
0.8832	High Similarity	NPC473399
0.8819	High Similarity	NPC165260
0.8819	High Similarity	NPC161239
0.8819	High Similarity	NPC7095
0.8819	High Similarity	NPC198455
0.8819	High Similarity	NPC112216
0.8819	High Similarity	NPC91730
0.8811	High Similarity	NPC281717
0.8803	High Similarity	NPC472556
0.8794	High Similarity	NPC477894
0.8784	High Similarity	NPC469399
0.8776	High Similarity	NPC217091
0.8776	High Similarity	NPC106895
0.8767	High Similarity	NPC469477
0.8767	High Similarity	NPC133430
0.8759	High Similarity	NPC197037
0.875	High Similarity	NPC266265
0.875	High Similarity	NPC92293
0.875	High Similarity	NPC471101
0.875	High Similarity	NPC301556
0.875	High Similarity	NPC476975
0.875	High Similarity	NPC270590
0.8732	High Similarity	NPC38696
0.8716	High Similarity	NPC472393
0.8716	High Similarity	NPC469417
0.8714	High Similarity	NPC475400
0.8707	High Similarity	NPC21410
0.8707	High Similarity	NPC5115
0.8707	High Similarity	NPC473670
0.869	High Similarity	NPC473214
0.869	High Similarity	NPC469448
0.869	High Similarity	NPC470245
0.8681	High Similarity	NPC132652
0.8662	High Similarity	NPC91703
0.8658	High Similarity	NPC471102
0.8643	High Similarity	NPC472395
0.8643	High Similarity	NPC472371
0.8639	High Similarity	NPC257213
0.8639	High Similarity	NPC158333
0.8639	High Similarity	NPC265395
0.8639	High Similarity	NPC256142
0.8639	High Similarity	NPC1173
0.8639	High Similarity	NPC472005
0.8639	High Similarity	NPC134685
0.8639	High Similarity	NPC77719
0.8639	High Similarity	NPC11588
0.8639	High Similarity	NPC304876
0.8639	High Similarity	NPC229545
0.8639	High Similarity	NPC249471
0.8639	High Similarity	NPC472030
0.8639	High Similarity	NPC248265
0.8639	High Similarity	NPC219419
0.8639	High Similarity	NPC472022
0.8639	High Similarity	NPC473414
0.8639	High Similarity	NPC242262
0.8639	High Similarity	NPC237549
0.8633	High Similarity	NPC472374
0.8633	High Similarity	NPC472372
0.8621	High Similarity	NPC473215
0.8613	High Similarity	NPC238370
0.8611	High Similarity	NPC473602
0.8611	High Similarity	NPC475552
0.8593	High Similarity	NPC195224
0.8582	High Similarity	NPC473082
0.8581	High Similarity	NPC112523
0.8581	High Similarity	NPC34066
0.8581	High Similarity	NPC132599
0.8581	High Similarity	NPC228204
0.8581	High Similarity	NPC469422
0.8581	High Similarity	NPC469730
0.8581	High Similarity	NPC114357
0.8581	High Similarity	NPC26033
0.8581	High Similarity	NPC473632
0.8581	High Similarity	NPC155329
0.8581	High Similarity	NPC114410
0.8581	High Similarity	NPC259144
0.8581	High Similarity	NPC473611
0.8561	High Similarity	NPC477893
0.854	High Similarity	NPC472418
0.8531	High Similarity	NPC477468
0.8531	High Similarity	NPC131966
0.8531	High Similarity	NPC191387
0.8521	High Similarity	NPC266374

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 NPC183270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	724
0.2-0.3	1432
0.3-0.4	2843
0.4-0.5	2291
0.5-0.6	1169
0.6-0.7	376
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7919	Intermediate Similarity	NPD7236	Approved
0.7888	Intermediate Similarity	NPD7799	Discontinued
0.7778	Intermediate Similarity	NPD7239	Suspended
0.7771	Intermediate Similarity	NPD8407	Phase 2
0.773	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8368	Discontinued
0.7692	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8434	Phase 2
0.7652	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8361	Approved
0.7485	Intermediate Similarity	NPD8360	Approved
0.7485	Intermediate Similarity	NPD8435	Approved
0.7482	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD2182	Approved
0.7346	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7058	Phase 2
0.7329	Intermediate Similarity	NPD7057	Phase 3
0.7267	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8485	Approved
0.7211	Intermediate Similarity	NPD7008	Discontinued
0.7209	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7819	Suspended
0.7162	Intermediate Similarity	NPD3764	Approved
0.7153	Intermediate Similarity	NPD6858	Approved
0.7153	Intermediate Similarity	NPD7094	Approved
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD7961	Discontinued
0.7111	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8166	Discontinued
0.7097	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7083	Intermediate Similarity	NPD7473	Discontinued
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7068	Intermediate Similarity	NPD164	Approved
0.705	Intermediate Similarity	NPD2629	Approved
0.7037	Intermediate Similarity	NPD37	Approved
0.7025	Intermediate Similarity	NPD2532	Approved
0.7025	Intermediate Similarity	NPD2533	Approved
0.7025	Intermediate Similarity	NPD2534	Approved
0.7019	Intermediate Similarity	NPD4380	Phase 2
0.7019	Intermediate Similarity	NPD6599	Discontinued
0.7014	Intermediate Similarity	NPD6287	Discontinued
0.7013	Intermediate Similarity	NPD2346	Discontinued
0.7012	Intermediate Similarity	NPD4966	Approved
0.7012	Intermediate Similarity	NPD4967	Phase 2
0.7012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4965	Approved
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD4198	Discontinued
0.7	Intermediate Similarity	NPD5844	Phase 1
0.6994	Remote Similarity	NPD5761	Phase 2
0.6994	Remote Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6994	Remote Similarity	NPD5760	Phase 2
0.6993	Remote Similarity	NPD5126	Approved
0.6993	Remote Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD3748	Approved
0.6985	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6273	Approved
0.6972	Remote Similarity	NPD7741	Discontinued
0.6957	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5402	Approved
0.6941	Remote Similarity	NPD7228	Approved
0.6937	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2067	Discontinued
0.6929	Remote Similarity	NPD5951	Approved
0.6928	Remote Similarity	NPD6234	Discontinued
0.6913	Remote Similarity	NPD6832	Phase 2
0.6903	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1238	Approved
0.6893	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6559	Discontinued
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7411	Suspended
0.6852	Remote Similarity	NPD7458	Discontinued
0.6852	Remote Similarity	NPD3226	Approved
0.6848	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3817	Phase 2
0.6839	Remote Similarity	NPD2438	Suspended
0.6839	Remote Similarity	NPD2796	Approved
0.6835	Remote Similarity	NPD6190	Approved
0.6832	Remote Similarity	NPD5403	Approved
0.6829	Remote Similarity	NPD6801	Discontinued
0.6818	Remote Similarity	NPD2567	Approved
0.6818	Remote Similarity	NPD2569	Approved
0.6813	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5401	Approved
0.6807	Remote Similarity	NPD7768	Phase 2
0.6789	Remote Similarity	NPD8462	Phase 1
0.6788	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6765	Approved
0.6782	Remote Similarity	NPD7685	Pre-registration
0.6782	Remote Similarity	NPD6764	Approved
0.6782	Remote Similarity	NPD7240	Approved
0.6776	Remote Similarity	NPD7713	Phase 3
0.6774	Remote Similarity	NPD2799	Discontinued
0.6772	Remote Similarity	NPD7003	Approved
0.6772	Remote Similarity	NPD3750	Approved
0.677	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3749	Approved
0.675	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3818	Discontinued
0.6738	Remote Similarity	NPD6010	Discontinued
0.6731	Remote Similarity	NPD5405	Approved
0.6731	Remote Similarity	NPD5404	Approved
0.6731	Remote Similarity	NPD2935	Discontinued
0.6731	Remote Similarity	NPD5406	Approved
0.6731	Remote Similarity	NPD5408	Approved
0.673	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD920	Approved
0.6727	Remote Similarity	NPD1934	Approved
0.672	Remote Similarity	NPD7497	Discontinued
0.6711	Remote Similarity	NPD2313	Discontinued
0.671	Remote Similarity	NPD7097	Phase 1
0.6708	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.669	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD230	Phase 1
0.6688	Remote Similarity	NPD1933	Approved
0.6688	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7266	Discontinued
0.6684	Remote Similarity	NPD8320	Phase 1
0.6684	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7610	Discontinued
0.6649	Remote Similarity	NPD8404	Phase 2
0.6648	Remote Similarity	NPD6534	Approved
0.6648	Remote Similarity	NPD6535	Approved
0.6647	Remote Similarity	NPD6959	Discontinued
0.6647	Remote Similarity	NPD5353	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5667	Approved
0.6643	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3317	Approved
0.6631	Remote Similarity	NPD7435	Discontinued
0.663	Remote Similarity	NPD7699	Phase 2
0.663	Remote Similarity	NPD7700	Phase 2
0.6629	Remote Similarity	NPD6785	Approved
0.6629	Remote Similarity	NPD6784	Approved
0.6628	Remote Similarity	NPD6166	Phase 2
0.6628	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD919	Approved
0.6623	Remote Similarity	NPD5736	Approved
0.6623	Remote Similarity	NPD2979	Phase 3
0.6609	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7054	Approved
0.6608	Remote Similarity	NPD5711	Approved
0.6608	Remote Similarity	NPD5710	Approved
0.6607	Remote Similarity	NPD3882	Suspended
0.6606	Remote Similarity	NPD7028	Phase 2
0.6605	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2800	Approved
0.6595	Remote Similarity	NPD8285	Discontinued
0.6594	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1465	Phase 2
0.6587	Remote Similarity	NPD8455	Phase 2
0.6582	Remote Similarity	NPD1471	Phase 3
0.6581	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6355	Discontinued
0.6571	Remote Similarity	NPD7472	Approved
0.657	Remote Similarity	NPD3926	Phase 2
0.6566	Remote Similarity	NPD6385	Approved
0.6566	Remote Similarity	NPD6386	Approved
0.6562	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4110	Phase 3
0.6556	Remote Similarity	NPD2798	Approved
0.6556	Remote Similarity	NPD6085	Phase 2
0.6556	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3751	Discontinued
0.6543	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1549	Phase 2
0.6534	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7115	Discovery
0.6519	Remote Similarity	NPD6100	Approved
0.6519	Remote Similarity	NPD1551	Phase 2
0.6519	Remote Similarity	NPD7798	Approved
0.6519	Remote Similarity	NPD6099	Approved
0.6516	Remote Similarity	NPD4307	Phase 2
0.651	Remote Similarity	NPD3972	Approved
0.651	Remote Similarity	NPD6637	Approved
0.6507	Remote Similarity	NPD9545	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