NPASS Compound

Structure

NPC157816 OpenBabel07101719512D 36 38 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 6.0622 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 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 -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 -1.7321 -3.0000 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 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 -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 2 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 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 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 -3.4641 -1.0000 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 -1.7321 0.0000 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 33 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 14 1 0 0 0 0 4 7 2 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 26 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 34 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 18 35 1 0 0 0 0 19 33 1 0 0 0 0 20 13 1 1 0 0 0 20 22 1 0 0 0 0 20 36 1 0 0 0 0 21 29 2 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 24 1 0 0 0 0 23 31 1 1 0 0 0 24 25 1 0 0 0 0 24 32 1 6 0 0 0 25 35 1 1 0 0 0 25 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.16
Volume:	488.251
LogP:	1.318
LogD:	1.129
LogS:	-3.014
# Rotatable Bonds:	10
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	3.967
Fsp3:	0.32
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.946
MDCK Permeability:	1.280247943213908e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.692
20% Bioavailability (F20%):	0.296
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.218
Plasma Protein Binding (PPB):	96.22100067138672%
Volume Distribution (VD):	0.323
Pgp-substrate:	3.5457327365875244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.323
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	5.465
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.157
AMES Toxicity:	0.557
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.958
Carcinogencity:	0.422
Eye Corrosion:	0.003
Eye Irritation:	0.069
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC157816

Natural Product ID:	NPC157816
*Common Name:**	Khainaoside C
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	OVXNLDIJUODSJZ-WNTHUPNMSA-N
Standard InCHI:	InChI=1S/C25H28O11/c1-33-19-12-14(3-2-10-26)5-8-18(19)35-25-24(32)23(31)22(30)20(36-25)13-34-21(29)9-6-15-4-7-16(27)17(28)11-15/h2-9,11-12,20,22-28,30-32H,10,13H2,1H3/b3-2+,9-6+/t20-,22-,23+,24-,25-/m1/s1
SMILES:	OC/C=C/c1ccc(c(c1)OC)O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087168
PubChem CID:	44606239
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	4.0	uM	PMID[551703]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	5.0	uM	PMID[551703]
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	0.1	uM	PMID[551703]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[551703]
NPT396	Cell Line	T47D	Homo sapiens	Inhibition	>	90.0	%	PMID[551703]

☑ 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 NPC157816 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	310
0.1-0.2	1488
0.2-0.3	4098
0.3-0.4	9441
0.4-0.5	8790
0.5-0.6	4778
0.6-0.7	7937
0.7-0.8	4788
0.8-0.85	674
0.85-0.9	288
0.9-0.95	92
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC478239
0.9778	High Similarity	NPC186406
0.9776	High Similarity	NPC100389
0.971	High Similarity	NPC476865
0.971	High Similarity	NPC199928
0.9708	High Similarity	NPC232228
0.9706	High Similarity	NPC140502
0.9704	High Similarity	NPC202700
0.9638	High Similarity	NPC476868
0.9638	High Similarity	NPC476866
0.9638	High Similarity	NPC476869
0.9638	High Similarity	NPC476864
0.9627	High Similarity	NPC37468
0.9627	High Similarity	NPC157554
0.9627	High Similarity	NPC186418
0.9571	High Similarity	NPC478237
0.9565	High Similarity	NPC110063
0.9565	High Similarity	NPC292443
0.9565	High Similarity	NPC476867
0.9504	High Similarity	NPC106138
0.9496	High Similarity	NPC216819
0.9496	High Similarity	NPC262182
0.9496	High Similarity	NPC287615
0.9496	High Similarity	NPC252292
0.9496	High Similarity	NPC476382
0.9496	High Similarity	NPC100998
0.9496	High Similarity	NPC83743
0.9496	High Similarity	NPC34927
0.9496	High Similarity	NPC34587
0.9485	High Similarity	NPC226005
0.9412	High Similarity	NPC126206
0.9362	High Similarity	NPC232992
0.9338	High Similarity	NPC471664
0.9338	High Similarity	NPC471665
0.9301	High Similarity	NPC476871
0.9296	High Similarity	NPC80732
0.9296	High Similarity	NPC199311
0.9296	High Similarity	NPC192763
0.9296	High Similarity	NPC3460
0.9296	High Similarity	NPC261122
0.9296	High Similarity	NPC210611
0.9296	High Similarity	NPC201148
0.9296	High Similarity	NPC300262
0.9296	High Similarity	NPC215095
0.9296	High Similarity	NPC28651
0.927	High Similarity	NPC470413
0.927	High Similarity	NPC138738
0.9265	High Similarity	NPC55040
0.9265	High Similarity	NPC476870
0.9231	High Similarity	NPC259347
0.9231	High Similarity	NPC90896
0.9231	High Similarity	NPC111785
0.9231	High Similarity	NPC306890
0.9231	High Similarity	NPC471062
0.9231	High Similarity	NPC283839
0.9231	High Similarity	NPC476398
0.9231	High Similarity	NPC94871
0.9231	High Similarity	NPC476386
0.9231	High Similarity	NPC473427
0.9231	High Similarity	NPC470933
0.9203	High Similarity	NPC98777
0.9203	High Similarity	NPC212770
0.9191	High Similarity	NPC886
0.9191	High Similarity	NPC135127
0.9191	High Similarity	NPC34293
0.9191	High Similarity	NPC287597
0.9185	High Similarity	NPC473285
0.9178	High Similarity	NPC194095
0.9178	High Similarity	NPC327032
0.9178	High Similarity	NPC191046
0.9167	High Similarity	NPC470934
0.9167	High Similarity	NPC257970
0.9167	High Similarity	NPC470927
0.9167	High Similarity	NPC188393
0.9161	High Similarity	NPC93924
0.9149	High Similarity	NPC297342
0.9143	High Similarity	NPC145319
0.913	High Similarity	NPC65530
0.913	High Similarity	NPC78363
0.913	High Similarity	NPC59324
0.913	High Similarity	NPC124149
0.911	High Similarity	NPC150442
0.911	High Similarity	NPC157898
0.9104	High Similarity	NPC477294
0.9104	High Similarity	NPC248355
0.9104	High Similarity	NPC477293
0.9104	High Similarity	NPC307110
0.9104	High Similarity	NPC229784
0.9103	High Similarity	NPC143480
0.9103	High Similarity	NPC85192
0.9103	High Similarity	NPC213197
0.9103	High Similarity	NPC7145
0.9103	High Similarity	NPC125823
0.9097	High Similarity	NPC478242
0.9091	High Similarity	NPC41844
0.9071	High Similarity	NPC476385
0.9071	High Similarity	NPC134405
0.9065	High Similarity	NPC197316
0.9065	High Similarity	NPC64141
0.9065	High Similarity	NPC472350
0.9065	High Similarity	NPC89105
0.9065	High Similarity	NPC81515
0.9065	High Similarity	NPC68092
0.9065	High Similarity	NPC476383
0.9058	High Similarity	NPC242028
0.9058	High Similarity	NPC199459
0.9058	High Similarity	NPC177035
0.9058	High Similarity	NPC52277
0.9058	High Similarity	NPC203230
0.9058	High Similarity	NPC166180
0.9054	High Similarity	NPC11411
0.9054	High Similarity	NPC471405
0.9051	High Similarity	NPC187194
0.9041	High Similarity	NPC169404
0.9041	High Similarity	NPC176186
0.9041	High Similarity	NPC36130
0.9041	High Similarity	NPC289967
0.9041	High Similarity	NPC472612
0.9041	High Similarity	NPC134905
0.9041	High Similarity	NPC472611
0.9041	High Similarity	NPC478268
0.9041	High Similarity	NPC53587
0.903	High Similarity	NPC232880
0.903	High Similarity	NPC302378
0.9007	High Similarity	NPC469559
0.9007	High Similarity	NPC222433
0.9007	High Similarity	NPC189115
0.9007	High Similarity	NPC475084
0.9007	High Similarity	NPC265648
0.9	High Similarity	NPC210478
0.9	High Similarity	NPC106944
0.8993	High Similarity	NPC133984
0.8993	High Similarity	NPC260425
0.8986	High Similarity	NPC214729
0.8986	High Similarity	NPC10205
0.8986	High Similarity	NPC185778
0.8978	High Similarity	NPC254398
0.8971	High Similarity	NPC219677
0.8971	High Similarity	NPC65942
0.8971	High Similarity	NPC248307
0.8966	High Similarity	NPC313334
0.8966	High Similarity	NPC212670
0.8966	High Similarity	NPC206264
0.8963	High Similarity	NPC295970
0.8963	High Similarity	NPC166040
0.8955	High Similarity	NPC476873
0.8951	High Similarity	NPC473909
0.8951	High Similarity	NPC143120
0.8951	High Similarity	NPC274960
0.8944	High Similarity	NPC185307
0.8944	High Similarity	NPC46092
0.8944	High Similarity	NPC470950
0.8936	High Similarity	NPC476377
0.8936	High Similarity	NPC47471
0.8936	High Similarity	NPC469661
0.8933	High Similarity	NPC160780
0.8933	High Similarity	NPC478269
0.8933	High Similarity	NPC289811
0.8929	High Similarity	NPC328273
0.8929	High Similarity	NPC205195
0.8929	High Similarity	NPC171134
0.8929	High Similarity	NPC321638
0.8929	High Similarity	NPC321184
0.8926	High Similarity	NPC228357
0.8913	High Similarity	NPC249791
0.8913	High Similarity	NPC471883
0.8913	High Similarity	NPC476411
0.8913	High Similarity	NPC476387
0.8913	High Similarity	NPC237594
0.8913	High Similarity	NPC35731
0.8913	High Similarity	NPC119060
0.8912	High Similarity	NPC476352
0.8912	High Similarity	NPC215060
0.8905	High Similarity	NPC473924
0.8905	High Similarity	NPC252833
0.8897	High Similarity	NPC80600
0.8897	High Similarity	NPC472024
0.8897	High Similarity	NPC96294
0.8897	High Similarity	NPC187398
0.8897	High Similarity	NPC476348
0.8881	High Similarity	NPC25292
0.8881	High Similarity	NPC471157
0.8881	High Similarity	NPC129417
0.8881	High Similarity	NPC473045
0.8881	High Similarity	NPC470235
0.8881	High Similarity	NPC283995
0.8874	High Similarity	NPC239966
0.8874	High Similarity	NPC203020
0.8874	High Similarity	NPC44507
0.8873	High Similarity	NPC473873
0.8873	High Similarity	NPC476356
0.8873	High Similarity	NPC473792
0.8873	High Similarity	NPC278469
0.8873	High Similarity	NPC193722
0.8867	High Similarity	NPC223335
0.8867	High Similarity	NPC1913
0.8867	High Similarity	NPC40920
0.8865	High Similarity	NPC473799
0.8865	High Similarity	NPC475530
0.8857	High Similarity	NPC476376

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 NPC157816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	832
0.2-0.3	1803
0.3-0.4	2826
0.4-0.5	1802
0.5-0.6	965
0.6-0.7	568
0.7-0.8	90
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9065	High Similarity	NPD7266	Discontinued
0.8966	High Similarity	NPD1653	Approved
0.8156	Intermediate Similarity	NPD3027	Phase 3
0.8137	Intermediate Similarity	NPD7054	Approved
0.8116	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7685	Pre-registration
0.8086	Intermediate Similarity	NPD7472	Approved
0.8086	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD3818	Discontinued
0.8049	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1091	Approved
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6190	Approved
0.7927	Intermediate Similarity	NPD6797	Phase 2
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7862	Intermediate Similarity	NPD6234	Discontinued
0.7853	Intermediate Similarity	NPD7228	Approved
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.78	Intermediate Similarity	NPD6674	Discontinued
0.7799	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7771	Intermediate Similarity	NPD37	Approved
0.7762	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1357	Approved
0.7736	Intermediate Similarity	NPD4965	Approved
0.7736	Intermediate Similarity	NPD4967	Phase 2
0.7736	Intermediate Similarity	NPD4966	Approved
0.7665	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD7199	Phase 2
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD8455	Phase 2
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5536	Phase 2
0.7589	Intermediate Similarity	NPD3705	Approved
0.7588	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7455	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD4340	Discontinued
0.745	Intermediate Similarity	NPD1933	Approved
0.7432	Intermediate Similarity	NPD6233	Phase 2
0.7426	Intermediate Similarity	NPD228	Approved
0.7419	Intermediate Similarity	NPD5058	Phase 3
0.7407	Intermediate Similarity	NPD3882	Suspended
0.7397	Intermediate Similarity	NPD2861	Phase 2
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7388	Intermediate Similarity	NPD1358	Approved
0.7381	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8313	Approved
0.7368	Intermediate Similarity	NPD8312	Approved
0.7362	Intermediate Similarity	NPD7075	Discontinued
0.7361	Intermediate Similarity	NPD2983	Phase 2
0.7361	Intermediate Similarity	NPD2982	Phase 2
0.7353	Intermediate Similarity	NPD7240	Approved
0.7351	Intermediate Similarity	NPD7097	Phase 1
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7333	Intermediate Similarity	NPD8127	Discontinued
0.7297	Intermediate Similarity	NPD7095	Approved
0.7296	Intermediate Similarity	NPD3687	Approved
0.7296	Intermediate Similarity	NPD3686	Approved
0.7292	Intermediate Similarity	NPD2981	Phase 2
0.7284	Intermediate Similarity	NPD2978	Approved
0.7284	Intermediate Similarity	NPD2977	Approved
0.7279	Intermediate Similarity	NPD9494	Approved
0.7273	Intermediate Similarity	NPD3496	Discontinued
0.7267	Intermediate Similarity	NPD1558	Phase 1
0.7261	Intermediate Similarity	NPD1511	Approved
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7239	Intermediate Similarity	NPD5402	Approved
0.7237	Intermediate Similarity	NPD4536	Approved
0.7237	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4538	Approved
0.723	Intermediate Similarity	NPD4908	Phase 1
0.7226	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD447	Suspended
0.7205	Intermediate Similarity	NPD4380	Phase 2
0.7194	Intermediate Similarity	NPD5283	Phase 1
0.7185	Intermediate Similarity	NPD3134	Approved
0.7179	Intermediate Similarity	NPD4110	Phase 3
0.7179	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6653	Approved
0.717	Intermediate Similarity	NPD1512	Approved
0.7162	Intermediate Similarity	NPD3018	Phase 2
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4357	Discontinued
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD7039	Approved
0.7133	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5403	Approved
0.7122	Intermediate Similarity	NPD5535	Approved
0.7122	Intermediate Similarity	NPD7843	Approved
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD6801	Discontinued
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7549	Discontinued
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7103	Intermediate Similarity	NPD1610	Phase 2
0.7102	Intermediate Similarity	NPD6842	Approved
0.7102	Intermediate Similarity	NPD6841	Approved
0.7102	Intermediate Similarity	NPD6843	Phase 3
0.7097	Intermediate Similarity	NPD5762	Approved
0.7097	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD7157	Approved
0.7086	Intermediate Similarity	NPD4062	Phase 3
0.7083	Intermediate Similarity	NPD6232	Discontinued
0.708	Intermediate Similarity	NPD2684	Approved
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5588	Approved
0.7078	Intermediate Similarity	NPD5960	Phase 3
0.7078	Intermediate Similarity	NPD7033	Discontinued
0.7075	Intermediate Similarity	NPD3225	Approved
0.7073	Intermediate Similarity	NPD7819	Suspended
0.7063	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1548	Phase 1
0.7044	Intermediate Similarity	NPD6799	Approved
0.7039	Intermediate Similarity	NPD4140	Approved
0.7033	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2935	Discontinued
0.7015	Intermediate Similarity	NPD291	Approved
0.7014	Intermediate Similarity	NPD5585	Approved
0.7013	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD290	Approved
0.7006	Intermediate Similarity	NPD3060	Approved
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD3536	Discontinued
0.7	Intermediate Similarity	NPD4123	Phase 3
0.6987	Remote Similarity	NPD1375	Discontinued
0.6982	Remote Similarity	NPD3787	Discontinued
0.6973	Remote Similarity	NPD7680	Approved
0.6966	Remote Similarity	NPD1778	Approved
0.6964	Remote Similarity	NPD5494	Approved
0.6962	Remote Similarity	NPD8166	Discontinued
0.6962	Remote Similarity	NPD3750	Approved
0.6962	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7473	Discontinued
0.6951	Remote Similarity	NPD6386	Approved
0.6951	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD7411	Suspended
0.6948	Remote Similarity	NPD2492	Phase 1
0.6943	Remote Similarity	NPD1549	Phase 2
0.6943	Remote Similarity	NPD2424	Discontinued
0.6939	Remote Similarity	NPD1608	Approved
0.6934	Remote Similarity	NPD968	Approved
0.6933	Remote Similarity	NPD3455	Phase 2
0.6932	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6032	Approved
0.6923	Remote Similarity	NPD1551	Phase 2
0.6913	Remote Similarity	NPD2797	Approved
0.6909	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3022	Approved
0.6906	Remote Similarity	NPD3021	Approved
0.6906	Remote Similarity	NPD556	Approved
0.6899	Remote Similarity	NPD4236	Phase 3
0.6899	Remote Similarity	NPD4237	Approved
0.6899	Remote Similarity	NPD4162	Approved
0.689	Remote Similarity	NPD4675	Approved
0.689	Remote Similarity	NPD4678	Approved
0.6879	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1535	Discovery
0.6867	Remote Similarity	NPD6584	Phase 3
0.6867	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4108	Discontinued
0.6855	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6671	Approved
0.6852	Remote Similarity	NPD6273	Approved
0.6852	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5846	Approved
0.6849	Remote Similarity	NPD5125	Phase 3
0.6849	Remote Similarity	NPD4626	Approved
0.6849	Remote Similarity	NPD6516	Phase 2
0.6849	Remote Similarity	NPD5126	Approved
0.6846	Remote Similarity	NPD8651	Approved
0.6845	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4625	Phase 3
0.6829	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7458	Discontinued
0.6828	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