NPASS Compound

Structure

NPC179914 OpenBabel07101719122D 39 42 0 0 1 0 0 0 0 0999 V2000 -2.1369 3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3005 -0.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8005 0.8506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3005 -0.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3005 1.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 1.6691 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3005 1.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 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 -8.3005 -0.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8005 0.8506 0.0000 C 0 0 0 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 -5.3005 3.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8005 -0.8814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8005 4.3147 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8005 0.8506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 3.4487 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 35 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 19 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 16 1 0 0 0 0 9 27 1 0 0 0 0 10 14 2 0 0 0 0 10 36 1 0 0 0 0 11 1 1 1 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 13 8 1 1 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 28 1 0 0 0 0 16 37 1 6 0 0 0 17 35 1 0 0 0 0 18 9 1 1 0 0 0 18 21 1 0 0 0 0 18 38 1 0 0 0 0 19 29 2 0 0 0 0 19 37 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 36 1 0 0 0 0 25 39 1 0 0 0 0 26 38 1 0 0 0 0 26 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.18
Volume:	519.844
LogP:	1.37
LogD:	0.604
LogS:	-2.0
# Rotatable Bonds:	9
TPSA:	201.67
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.182
Synthetic Accessibility Score:	4.811
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.391
MDCK Permeability:	7.579550583614036e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.515
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.362
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	70.07402038574219%
Volume Distribution (VD):	0.315
Pgp-substrate:	20.865463256835938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	1.87
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.504
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC179914

Natural Product ID:	NPC179914
*Common Name:**	Khainaoside B
IUPAC Name:	(1S,4aS,6S,7S,7aS)-6-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Synonyms:
Standard InCHIKey:	DVNQRYDJAAFJBQ-GBLWNDTNSA-N
Standard InCHI:	InChI=1S/C26H32O13/c1-11-16(37-19(29)6-4-12-3-5-15(28)17(7-12)35-2)8-13-14(24(33)34)10-36-25(20(11)13)39-26-23(32)22(31)21(30)18(9-27)38-26/h3-7,10-11,13,16,18,20-23,25-28,30-32H,8-9H2,1-2H3,(H,33,34)/b6-4+/t11-,13-,16+,18-,20-,21-,22+,23-,25+,26+/m1/s1
SMILES:	C[C@@H]1[C@H](C[C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)O)OC(=O)/C=C/c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077079
PubChem CID:	44606238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO25391	Vitex glabrata	Species	Lamiaceae	Eukaryota	leaves	Chantaburi Province, Thailand	2007-Nov	PMID[19943620]
NPO25391	Vitex glabrata	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	0.1	uM	PMID[558162]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[558162]
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	0.1	uM	PMID[558162]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[558162]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	>	90.0	%	PMID[558162]
NPT396	Cell Line	T47D	Homo sapiens	Inhibition	>	90.0	%	PMID[558162]

☑ 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 NPC179914 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	339
0.1-0.2	1237
0.2-0.3	2754
0.3-0.4	5684
0.4-0.5	10220
0.5-0.6	7824
0.6-0.7	8502
0.7-0.8	5519
0.8-0.85	500
0.85-0.9	93
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC475484
0.9494	High Similarity	NPC21956
0.9423	High Similarity	NPC476011
0.9342	High Similarity	NPC203664
0.9299	High Similarity	NPC145847
0.9295	High Similarity	NPC474936
0.9276	High Similarity	NPC269914
0.9276	High Similarity	NPC478249
0.9276	High Similarity	NPC475379
0.9245	High Similarity	NPC301910
0.9245	High Similarity	NPC130730
0.9241	High Similarity	NPC109990
0.9231	High Similarity	NPC469384
0.9167	High Similarity	NPC475663
0.9167	High Similarity	NPC286919
0.9145	High Similarity	NPC96599
0.9103	High Similarity	NPC478248
0.9085	High Similarity	NPC117346
0.9085	High Similarity	NPC240592
0.9085	High Similarity	NPC147224
0.9079	High Similarity	NPC308178
0.9067	High Similarity	NPC202391
0.9067	High Similarity	NPC296659
0.9057	High Similarity	NPC206815
0.9045	High Similarity	NPC187205
0.9032	High Similarity	NPC229548
0.9032	High Similarity	NPC478241
0.9032	High Similarity	NPC89693
0.9026	High Similarity	NPC289021
0.9026	High Similarity	NPC158546
0.9006	High Similarity	NPC282551
0.8931	High Similarity	NPC138993
0.8924	High Similarity	NPC226759
0.891	High Similarity	NPC61604
0.891	High Similarity	NPC299706
0.891	High Similarity	NPC115466
0.891	High Similarity	NPC245615
0.8896	High Similarity	NPC478242
0.8868	High Similarity	NPC76211
0.8839	High Similarity	NPC69367
0.8827	High Similarity	NPC180586
0.8816	High Similarity	NPC184464
0.8816	High Similarity	NPC251062
0.8812	High Similarity	NPC478265
0.8808	High Similarity	NPC296643
0.8797	High Similarity	NPC38699
0.879	High Similarity	NPC44730
0.8788	High Similarity	NPC470685
0.8774	High Similarity	NPC478234
0.8774	High Similarity	NPC478236
0.8766	High Similarity	NPC473149
0.875	High Similarity	NPC475213
0.875	High Similarity	NPC152796
0.875	High Similarity	NPC186296
0.8742	High Similarity	NPC471405
0.8742	High Similarity	NPC163635
0.8734	High Similarity	NPC194095
0.8734	High Similarity	NPC191046
0.8734	High Similarity	NPC478232
0.8734	High Similarity	NPC327032
0.8726	High Similarity	NPC478268
0.872	High Similarity	NPC208818
0.8718	High Similarity	NPC229882
0.8718	High Similarity	NPC158635
0.8688	High Similarity	NPC472860
0.8684	High Similarity	NPC140502
0.8679	High Similarity	NPC131532
0.8679	High Similarity	NPC10205
0.8671	High Similarity	NPC157898
0.865	High Similarity	NPC100420
0.8645	High Similarity	NPC18789
0.8636	High Similarity	NPC34587
0.8636	High Similarity	NPC100998
0.8636	High Similarity	NPC476382
0.8636	High Similarity	NPC34927
0.8636	High Similarity	NPC252292
0.8627	High Similarity	NPC88754
0.8627	High Similarity	NPC116104
0.8627	High Similarity	NPC302286
0.8627	High Similarity	NPC237872
0.8627	High Similarity	NPC263397
0.8625	High Similarity	NPC228357
0.8625	High Similarity	NPC478055
0.8625	High Similarity	NPC475378
0.8623	High Similarity	NPC316539
0.8618	High Similarity	NPC137501
0.8618	High Similarity	NPC7518
0.8618	High Similarity	NPC154262
0.8618	High Similarity	NPC159387
0.8609	High Similarity	NPC226005
0.8608	High Similarity	NPC36130
0.8608	High Similarity	NPC478235
0.8608	High Similarity	NPC134905
0.8608	High Similarity	NPC194705
0.8608	High Similarity	NPC267091
0.8606	High Similarity	NPC286809
0.86	High Similarity	NPC157554
0.8599	High Similarity	NPC205054
0.8598	High Similarity	NPC475738
0.8589	High Similarity	NPC41009
0.8581	High Similarity	NPC474234
0.858	High Similarity	NPC239966
0.858	High Similarity	NPC203020
0.8571	High Similarity	NPC133984
0.8571	High Similarity	NPC473281
0.8571	High Similarity	NPC77922
0.8571	High Similarity	NPC110063
0.8571	High Similarity	NPC49173
0.8553	High Similarity	NPC229354
0.8553	High Similarity	NPC137813
0.8544	High Similarity	NPC243891
0.8535	High Similarity	NPC111785
0.8526	High Similarity	NPC232992
0.8519	High Similarity	NPC160780
0.8519	High Similarity	NPC469654
0.8519	High Similarity	NPC289811
0.8516	High Similarity	NPC216819
0.8516	High Similarity	NPC262182
0.8516	High Similarity	NPC83743
0.8516	High Similarity	NPC287615
0.8514	High Similarity	NPC475299
0.8509	High Similarity	NPC11411
0.8509	High Similarity	NPC478266
0.8506	High Similarity	NPC478239
0.85	High Similarity	NPC476364
0.8497	Intermediate Similarity	NPC472711
0.8487	Intermediate Similarity	NPC220936
0.8487	Intermediate Similarity	NPC31745
0.8487	Intermediate Similarity	NPC100389
0.8481	Intermediate Similarity	NPC470934
0.8481	Intermediate Similarity	NPC188393
0.8471	Intermediate Similarity	NPC23677
0.8471	Intermediate Similarity	NPC98009
0.8471	Intermediate Similarity	NPC116229
0.8466	Intermediate Similarity	NPC44507
0.8462	Intermediate Similarity	NPC119773
0.8462	Intermediate Similarity	NPC469354
0.8462	Intermediate Similarity	NPC474268
0.8462	Intermediate Similarity	NPC469438
0.8462	Intermediate Similarity	NPC473867
0.8462	Intermediate Similarity	NPC143246
0.8462	Intermediate Similarity	NPC37838
0.8462	Intermediate Similarity	NPC475539
0.8457	Intermediate Similarity	NPC223335
0.8457	Intermediate Similarity	NPC1913
0.8457	Intermediate Similarity	NPC104275
0.8457	Intermediate Similarity	NPC40920
0.8457	Intermediate Similarity	NPC4747
0.8452	Intermediate Similarity	NPC478240
0.8452	Intermediate Similarity	NPC297342
0.8447	Intermediate Similarity	NPC172920
0.8447	Intermediate Similarity	NPC156624
0.8442	Intermediate Similarity	NPC157816
0.8442	Intermediate Similarity	NPC52664
0.8439	Intermediate Similarity	NPC299855
0.8439	Intermediate Similarity	NPC96194
0.8438	Intermediate Similarity	NPC310661
0.8438	Intermediate Similarity	NPC105827
0.8431	Intermediate Similarity	NPC202700
0.843	Intermediate Similarity	NPC473776
0.843	Intermediate Similarity	NPC473205
0.8421	Intermediate Similarity	NPC304152
0.8418	Intermediate Similarity	NPC106138
0.8418	Intermediate Similarity	NPC476398
0.8418	Intermediate Similarity	NPC476394
0.8418	Intermediate Similarity	NPC259347
0.8418	Intermediate Similarity	NPC473427
0.8418	Intermediate Similarity	NPC470933
0.8418	Intermediate Similarity	NPC98809
0.8418	Intermediate Similarity	NPC471062
0.8418	Intermediate Similarity	NPC306890
0.8418	Intermediate Similarity	NPC476386
0.8418	Intermediate Similarity	NPC94871
0.8415	Intermediate Similarity	NPC311803
0.8415	Intermediate Similarity	NPC472859
0.8415	Intermediate Similarity	NPC25389
0.8405	Intermediate Similarity	NPC478269
0.8397	Intermediate Similarity	NPC475528
0.8397	Intermediate Similarity	NPC469683
0.8391	Intermediate Similarity	NPC189704
0.8387	Intermediate Similarity	NPC470950
0.8387	Intermediate Similarity	NPC477898
0.8387	Intermediate Similarity	NPC293154
0.8387	Intermediate Similarity	NPC185307
0.8383	Intermediate Similarity	NPC298847
0.8377	Intermediate Similarity	NPC100675
0.8377	Intermediate Similarity	NPC186406
0.8375	Intermediate Similarity	NPC289438
0.8375	Intermediate Similarity	NPC476434
0.8372	Intermediate Similarity	NPC188217
0.8366	Intermediate Similarity	NPC49597
0.8365	Intermediate Similarity	NPC257970
0.8365	Intermediate Similarity	NPC12006
0.8365	Intermediate Similarity	NPC470927
0.8364	Intermediate Similarity	NPC285108
0.8364	Intermediate Similarity	NPC148273
0.8364	Intermediate Similarity	NPC33298
0.8364	Intermediate Similarity	NPC246024
0.8355	Intermediate Similarity	NPC186418
0.8355	Intermediate Similarity	NPC52277

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 NPC179914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	784
0.2-0.3	1709
0.3-0.4	2565
0.4-0.5	2134
0.5-0.6	1111
0.6-0.7	482
0.7-0.8	77
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD7685	Pre-registration
0.8314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7266	Discontinued
0.8193	Intermediate Similarity	NPD7199	Phase 2
0.8166	Intermediate Similarity	NPD3818	Discontinued
0.8166	Intermediate Similarity	NPD7228	Approved
0.8165	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7054	Approved
0.8075	Intermediate Similarity	NPD1653	Approved
0.8072	Intermediate Similarity	NPD6234	Discontinued
0.807	Intermediate Similarity	NPD7074	Phase 3
0.807	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD37	Approved
0.7952	Intermediate Similarity	NPD4965	Approved
0.7952	Intermediate Similarity	NPD4967	Phase 2
0.7952	Intermediate Similarity	NPD4966	Approved
0.7931	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7251	Discontinued
0.787	Intermediate Similarity	NPD8127	Discontinued
0.7844	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7808	Phase 3
0.7816	Intermediate Similarity	NPD6797	Phase 2
0.7812	Intermediate Similarity	NPD6190	Approved
0.7798	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7240	Approved
0.7665	Intermediate Similarity	NPD1934	Approved
0.7651	Intermediate Similarity	NPD7028	Phase 2
0.7643	Intermediate Similarity	NPD6653	Approved
0.764	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD8455	Phase 2
0.7515	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6559	Discontinued
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD230	Phase 1
0.744	Intermediate Similarity	NPD4380	Phase 2
0.7436	Intermediate Similarity	NPD3027	Phase 3
0.7423	Intermediate Similarity	NPD4110	Phase 3
0.7423	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD2801	Approved
0.7412	Intermediate Similarity	NPD1465	Phase 2
0.7405	Intermediate Similarity	NPD3620	Phase 2
0.7405	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8312	Approved
0.7386	Intermediate Similarity	NPD7473	Discontinued
0.7384	Intermediate Similarity	NPD7075	Discontinued
0.7362	Intermediate Similarity	NPD6674	Discontinued
0.7358	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6005	Phase 3
0.7346	Intermediate Similarity	NPD6004	Phase 3
0.7346	Intermediate Similarity	NPD5762	Approved
0.7346	Intermediate Similarity	NPD5763	Approved
0.7346	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6002	Phase 3
0.734	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3882	Suspended
0.7317	Intermediate Similarity	NPD8166	Discontinued
0.7314	Intermediate Similarity	NPD6232	Discontinued
0.7308	Intermediate Similarity	NPD9494	Approved
0.7305	Intermediate Similarity	NPD6273	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7277	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3705	Approved
0.7253	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5647	Approved
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7819	Suspended
0.72	Intermediate Similarity	NPD5494	Approved
0.7195	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1613	Approved
0.7188	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1511	Approved
0.7168	Intermediate Similarity	NPD5353	Approved
0.7151	Intermediate Similarity	NPD6801	Discontinued
0.7125	Intermediate Similarity	NPD6663	Approved
0.7101	Intermediate Similarity	NPD1512	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7093	Intermediate Similarity	NPD6385	Approved
0.7093	Intermediate Similarity	NPD6386	Approved
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7089	Intermediate Similarity	NPD5736	Approved
0.7081	Intermediate Similarity	NPD4140	Approved
0.7081	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6362	Approved
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1357	Approved
0.7056	Intermediate Similarity	NPD7799	Discontinued
0.7056	Intermediate Similarity	NPD3751	Discontinued
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7048	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1091	Approved
0.7019	Intermediate Similarity	NPD6233	Phase 2
0.701	Intermediate Similarity	NPD7435	Discontinued
0.7006	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7930	Approved
0.6993	Remote Similarity	NPD9545	Approved
0.6989	Remote Similarity	NPD8434	Phase 2
0.6971	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5402	Approved
0.697	Remote Similarity	NPD2935	Discontinued
0.6962	Remote Similarity	NPD2797	Approved
0.6957	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD3268	Approved
0.6941	Remote Similarity	NPD2532	Approved
0.6941	Remote Similarity	NPD2533	Approved
0.6941	Remote Similarity	NPD2534	Approved
0.6939	Remote Similarity	NPD7999	Approved
0.6937	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1933	Approved
0.6933	Remote Similarity	NPD447	Suspended
0.6933	Remote Similarity	NPD5735	Approved
0.6927	Remote Similarity	NPD3787	Discontinued
0.6923	Remote Similarity	NPD7497	Discontinued
0.6919	Remote Similarity	NPD8151	Discontinued
0.6918	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD5761	Phase 2
0.6909	Remote Similarity	NPD1510	Phase 2
0.6905	Remote Similarity	NPD3750	Approved
0.6903	Remote Similarity	NPD17	Approved
0.6897	Remote Similarity	NPD7411	Suspended
0.6894	Remote Similarity	NPD7095	Approved
0.6889	Remote Similarity	NPD5242	Approved
0.6886	Remote Similarity	NPD1549	Phase 2
0.6882	Remote Similarity	NPD6799	Approved
0.6875	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4060	Phase 1
0.6867	Remote Similarity	NPD228	Approved
0.6867	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD2438	Suspended
0.6867	Remote Similarity	NPD6100	Approved
0.686	Remote Similarity	NPD5403	Approved
0.6856	Remote Similarity	NPD6780	Approved
0.6856	Remote Similarity	NPD6776	Approved
0.6856	Remote Similarity	NPD6782	Approved
0.6856	Remote Similarity	NPD6778	Approved
0.6856	Remote Similarity	NPD6779	Approved
0.6856	Remote Similarity	NPD6781	Approved
0.6856	Remote Similarity	NPD6777	Approved
0.6854	Remote Similarity	NPD919	Approved
0.6852	Remote Similarity	NPD3764	Approved
0.6845	Remote Similarity	NPD1652	Phase 2
0.6842	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7296	Approved
0.6842	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6599	Discontinued
0.6829	Remote Similarity	NPD5124	Phase 1
0.6829	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7236	Approved
0.6818	Remote Similarity	NPD5536	Phase 2
0.6812	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6765	Approved
0.6811	Remote Similarity	NPD7039	Approved
0.6811	Remote Similarity	NPD7038	Approved
0.6811	Remote Similarity	NPD6764	Approved
0.681	Remote Similarity	NPD8032	Phase 2
0.6809	Remote Similarity	NPD8150	Discontinued
0.68	Remote Similarity	NPD7874	Approved
0.68	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5958	Discontinued
0.6784	Remote Similarity	NPD7585	Approved
0.6782	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3455	Phase 2
0.678	Remote Similarity	NPD5977	Approved
0.678	Remote Similarity	NPD5978	Approved
0.6776	Remote Similarity	NPD5283	Phase 1
0.6772	Remote Similarity	NPD6841	Approved
0.6772	Remote Similarity	NPD6843	Phase 3
0.6772	Remote Similarity	NPD6842	Approved
0.6772	Remote Similarity	NPD9269	Phase 2
0.6766	Remote Similarity	NPD2796	Approved
0.6766	Remote Similarity	NPD7783	Phase 2
0.6766	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7697	Approved
0.6751	Remote Similarity	NPD7696	Phase 3
0.6751	Remote Similarity	NPD7698	Approved
0.675	Remote Similarity	NPD3094	Phase 2
0.6747	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5401	Approved
0.6744	Remote Similarity	NPD3146	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