NPASS Compound

Structure

CID328093 OpenBabel06191716202D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 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 -1.7321 -0.0000 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 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 0.8660 -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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -4.3301 2.5000 0.0000 C 0 0 3 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 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 -7.7942 4.5000 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 -1.7321 3.0000 0.0000 O 0 0 0 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 -0.8660 1.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 11 1 0 0 0 0 3 13 2 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 11 16 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 28 1 0 0 0 0 15 9 1 1 0 0 0 15 17 1 0 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 21 1 0 0 0 0 19 26 1 6 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 1 0 0 0 21 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.13
Volume:	398.203
LogP:	0.509
LogD:	0.599
LogS:	-2.587
# Rotatable Bonds:	4
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	3.912
Fsp3:	0.381
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:	-6.244
MDCK Permeability:	1.4505792933050543e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.667
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	89.12646484375%
Volume Distribution (VD):	0.706
Pgp-substrate:	6.992652416229248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.23
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	3.571
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.717
AMES Toxicity:	0.331
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.538
Carcinogencity:	0.723
Eye Corrosion:	0.003
Eye Irritation:	0.167
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC328093

Natural Product ID:	NPC328093
*Common Name:**	3-(4-Hydroxyphenyl)-8-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-3,4-Dihydroisochromen-1-One
IUPAC Name:	3-(4-hydroxyphenyl)-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroisochromen-1-one
Synonyms:	hydrangenol 8-O-glucoside
Standard InCHIKey:	IKTPWMTZNXOEIV-VRKGAULQSA-N
Standard InCHI:	InChI=1S/C21H22O9/c22-9-15-17(24)18(25)19(26)21(30-15)29-13-3-1-2-11-8-14(28-20(27)16(11)13)10-4-6-12(23)7-5-10/h1-7,14-15,17-19,21-26H,8-9H2/t14?,15-,17-,18+,19-,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cccc3c2C(=O)OC(C3)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL394399
PubChem CID:	13962962
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
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17609121]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16745	Scorzonera judaica	Species	Asteraceae	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
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	11.1	%	PMID[479485]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	1.2	%	PMID[479485]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	10.5	%	PMID[479485]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	9.2	%	PMID[479485]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	11.2	%	PMID[479485]

☑ 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 NPC328093 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	376
0.1-0.2	1515
0.2-0.3	3313
0.3-0.4	7604
0.4-0.5	9875
0.5-0.6	4857
0.6-0.7	5471
0.7-0.8	7309
0.8-0.85	1859
0.85-0.9	471
0.9-0.95	43
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC99216
0.9669	High Similarity	NPC185103
0.9618	High Similarity	NPC298847
0.9494	High Similarity	NPC249977
0.9367	High Similarity	NPC7752
0.9295	High Similarity	NPC308265
0.9255	High Similarity	NPC298778
0.9241	High Similarity	NPC22324
0.9236	High Similarity	NPC271479
0.9231	High Similarity	NPC177742
0.9226	High Similarity	NPC169248
0.9226	High Similarity	NPC39351
0.9226	High Similarity	NPC26195
0.9226	High Similarity	NPC72649
0.9226	High Similarity	NPC97052
0.9202	High Similarity	NPC63105
0.9193	High Similarity	NPC222455
0.9182	High Similarity	NPC29830
0.9167	High Similarity	NPC170475
0.9167	High Similarity	NPC206378
0.9167	High Similarity	NPC127406
0.9167	High Similarity	NPC261866
0.9136	High Similarity	NPC199079
0.9136	High Similarity	NPC210808
0.9119	High Similarity	NPC216752
0.9119	High Similarity	NPC472876
0.9114	High Similarity	NPC472320
0.9108	High Similarity	NPC43638
0.9108	High Similarity	NPC156457
0.9108	High Similarity	NPC313163
0.9108	High Similarity	NPC258035
0.9108	High Similarity	NPC161749
0.9108	High Similarity	NPC197896
0.9108	High Similarity	NPC257309
0.9097	High Similarity	NPC259182
0.9097	High Similarity	NPC121001
0.9096	High Similarity	NPC475161
0.9096	High Similarity	NPC477860
0.9085	High Similarity	NPC474345
0.9085	High Similarity	NPC3718
0.9085	High Similarity	NPC470454
0.9085	High Similarity	NPC68381
0.9085	High Similarity	NPC199533
0.908	High Similarity	NPC257011
0.908	High Similarity	NPC9002
0.908	High Similarity	NPC67134
0.908	High Similarity	NPC472386
0.908	High Similarity	NPC288152
0.908	High Similarity	NPC47140
0.908	High Similarity	NPC137871
0.9074	High Similarity	NPC259905
0.9068	High Similarity	NPC5778
0.9068	High Similarity	NPC70441
0.9068	High Similarity	NPC178851
0.9068	High Similarity	NPC236934
0.9057	High Similarity	NPC47923
0.9057	High Similarity	NPC303913
0.9057	High Similarity	NPC101636
0.9051	High Similarity	NPC43761
0.9051	High Similarity	NPC73511
0.9038	High Similarity	NPC29763
0.9038	High Similarity	NPC230439
0.9038	High Similarity	NPC279281
0.9038	High Similarity	NPC299761
0.9038	High Similarity	NPC210003
0.9038	High Similarity	NPC39360
0.9038	High Similarity	NPC83283
0.9038	High Similarity	NPC106625
0.9038	High Similarity	NPC92153
0.9038	High Similarity	NPC143851
0.9036	High Similarity	NPC84494
0.9036	High Similarity	NPC245059
0.903	High Similarity	NPC475246
0.9024	High Similarity	NPC213052
0.9012	High Similarity	NPC45400
0.9012	High Similarity	NPC92565
0.9012	High Similarity	NPC160156
0.9006	High Similarity	NPC178281
0.9	High Similarity	NPC259834
0.9	High Similarity	NPC300537
0.9	High Similarity	NPC101116
0.9	High Similarity	NPC56735
0.9	High Similarity	NPC189142
0.9	High Similarity	NPC298171
0.9	High Similarity	NPC61594
0.9	High Similarity	NPC77660
0.9	High Similarity	NPC44947
0.9	High Similarity	NPC212099
0.9	High Similarity	NPC127782
0.8994	High Similarity	NPC200708
0.8994	High Similarity	NPC97285
0.8994	High Similarity	NPC142860
0.8994	High Similarity	NPC153342
0.8994	High Similarity	NPC246469
0.8994	High Similarity	NPC271270
0.8987	High Similarity	NPC473512
0.8987	High Similarity	NPC65003
0.8987	High Similarity	NPC129827
0.8987	High Similarity	NPC44931
0.8982	High Similarity	NPC164047
0.8982	High Similarity	NPC470452
0.8982	High Similarity	NPC470453
0.8982	High Similarity	NPC470448
0.8981	High Similarity	NPC27408
0.8981	High Similarity	NPC99233
0.8981	High Similarity	NPC95090
0.8974	High Similarity	NPC88484
0.8974	High Similarity	NPC259767
0.8963	High Similarity	NPC76128
0.8963	High Similarity	NPC271385
0.8963	High Similarity	NPC30432
0.8963	High Similarity	NPC5029
0.8963	High Similarity	NPC111536
0.8957	High Similarity	NPC270578
0.8957	High Similarity	NPC293629
0.8957	High Similarity	NPC472383
0.8957	High Similarity	NPC43587
0.8957	High Similarity	NPC472381
0.8957	High Similarity	NPC170675
0.8957	High Similarity	NPC105283
0.8957	High Similarity	NPC112755
0.8957	High Similarity	NPC52382
0.8957	High Similarity	NPC471457
0.8957	High Similarity	NPC229687
0.8951	High Similarity	NPC115674
0.8951	High Similarity	NPC8856
0.8951	High Similarity	NPC210073
0.8944	High Similarity	NPC270335
0.8944	High Similarity	NPC124155
0.8944	High Similarity	NPC88023
0.8944	High Similarity	NPC19709
0.8944	High Similarity	NPC257566
0.8944	High Similarity	NPC309025
0.8944	High Similarity	NPC168822
0.8944	High Similarity	NPC243930
0.8944	High Similarity	NPC147596
0.8944	High Similarity	NPC191306
0.8944	High Similarity	NPC17432
0.8938	High Similarity	NPC477628
0.8938	High Similarity	NPC85707
0.8938	High Similarity	NPC224530
0.8938	High Similarity	NPC48093
0.8938	High Similarity	NPC472994
0.8938	High Similarity	NPC270675
0.8938	High Similarity	NPC210961
0.8938	High Similarity	NPC216496
0.8938	High Similarity	NPC159579
0.8938	High Similarity	NPC259957
0.8938	High Similarity	NPC477629
0.8938	High Similarity	NPC282169
0.8938	High Similarity	NPC195685
0.8938	High Similarity	NPC129217
0.8935	High Similarity	NPC241847
0.8931	High Similarity	NPC279732
0.8931	High Similarity	NPC138811
0.8931	High Similarity	NPC473634
0.8931	High Similarity	NPC22062
0.8924	High Similarity	NPC307938
0.8924	High Similarity	NPC203500
0.8924	High Similarity	NPC45165
0.8924	High Similarity	NPC323593
0.8917	High Similarity	NPC299435
0.8917	High Similarity	NPC260604
0.8916	High Similarity	NPC46958
0.8916	High Similarity	NPC472380
0.8916	High Similarity	NPC268533
0.8916	High Similarity	NPC472382
0.8916	High Similarity	NPC472384
0.891	High Similarity	NPC215921
0.891	High Similarity	NPC70016
0.8909	High Similarity	NPC199357
0.8902	High Similarity	NPC177731
0.8902	High Similarity	NPC149011
0.8902	High Similarity	NPC471416
0.8902	High Similarity	NPC105095
0.8902	High Similarity	NPC204937
0.8902	High Similarity	NPC231194
0.8902	High Similarity	NPC183357
0.8902	High Similarity	NPC79056
0.8902	High Similarity	NPC155763
0.8902	High Similarity	NPC78734
0.8902	High Similarity	NPC20505
0.8902	High Similarity	NPC51326
0.8902	High Similarity	NPC44558
0.8902	High Similarity	NPC21190
0.8902	High Similarity	NPC116864
0.8902	High Similarity	NPC34287
0.8902	High Similarity	NPC218488
0.8902	High Similarity	NPC44328
0.8902	High Similarity	NPC235260
0.8902	High Similarity	NPC244776
0.8902	High Similarity	NPC22195
0.8902	High Similarity	NPC150767
0.8896	High Similarity	NPC302989
0.8896	High Similarity	NPC116745
0.8896	High Similarity	NPC92054
0.8896	High Similarity	NPC477502
0.8896	High Similarity	NPC229729
0.8896	High Similarity	NPC93099
0.8896	High Similarity	NPC140722

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 NPC328093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	862
0.2-0.3	1704
0.3-0.4	2572
0.4-0.5	1926
0.5-0.6	1097
0.6-0.7	462
0.7-0.8	165
0.8-0.85	26
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9108	High Similarity	NPD4381	Clinical (unspecified phase)
0.8902	High Similarity	NPD7074	Phase 3
0.8841	High Similarity	NPD7054	Approved
0.8788	High Similarity	NPD7472	Approved
0.8743	High Similarity	NPD4338	Clinical (unspecified phase)
0.8735	High Similarity	NPD6797	Phase 2
0.8727	High Similarity	NPD7804	Clinical (unspecified phase)
0.869	High Similarity	NPD8313	Approved
0.869	High Similarity	NPD8312	Approved
0.8683	High Similarity	NPD7251	Discontinued
0.8667	High Similarity	NPD3818	Discontinued
0.8631	High Similarity	NPD7808	Phase 3
0.8491	Intermediate Similarity	NPD4380	Phase 2
0.8462	Intermediate Similarity	NPD6559	Discontinued
0.8457	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8434	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6166	Phase 2
0.8434	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7075	Discontinued
0.8385	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD8455	Phase 2
0.8253	Intermediate Similarity	NPD6959	Discontinued
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD1465	Phase 2
0.8194	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5844	Phase 1
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8171	Intermediate Similarity	NPD5402	Approved
0.816	Intermediate Similarity	NPD6801	Discontinued
0.8153	Intermediate Similarity	NPD4628	Phase 3
0.8141	Intermediate Similarity	NPD1549	Phase 2
0.8098	Intermediate Similarity	NPD7411	Suspended
0.8095	Intermediate Similarity	NPD6232	Discontinued
0.8081	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD7783	Phase 2
0.8075	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD3750	Approved
0.8036	Intermediate Similarity	NPD7199	Phase 2
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.7989	Intermediate Similarity	NPD7435	Discontinued
0.7988	Intermediate Similarity	NPD3787	Discontinued
0.7964	Intermediate Similarity	NPD3749	Approved
0.7953	Intermediate Similarity	NPD7473	Discontinued
0.795	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5401	Approved
0.795	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7685	Pre-registration
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7923	Intermediate Similarity	NPD6782	Approved
0.7923	Intermediate Similarity	NPD6780	Approved
0.7923	Intermediate Similarity	NPD6781	Approved
0.7923	Intermediate Similarity	NPD6777	Approved
0.7923	Intermediate Similarity	NPD6778	Approved
0.7923	Intermediate Similarity	NPD6776	Approved
0.7923	Intermediate Similarity	NPD6779	Approved
0.7921	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1512	Approved
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD8151	Discontinued
0.787	Intermediate Similarity	NPD5494	Approved
0.7866	Intermediate Similarity	NPD3226	Approved
0.7866	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7266	Discontinued
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7836	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1510	Phase 2
0.7831	Intermediate Similarity	NPD37	Approved
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7805	Intermediate Similarity	NPD1653	Approved
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD3882	Suspended
0.7798	Intermediate Similarity	NPD4965	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7798	Intermediate Similarity	NPD7768	Phase 2
0.7796	Intermediate Similarity	NPD7697	Approved
0.7796	Intermediate Similarity	NPD7698	Approved
0.7796	Intermediate Similarity	NPD7696	Phase 3
0.7785	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7874	Approved
0.7737	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2346	Discontinued
0.773	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7701	Phase 2
0.7722	Intermediate Similarity	NPD3748	Approved
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.766	Intermediate Similarity	NPD7870	Phase 2
0.766	Intermediate Similarity	NPD7871	Phase 2
0.766	Intermediate Similarity	NPD8320	Phase 1
0.766	Intermediate Similarity	NPD8319	Approved
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.765	Intermediate Similarity	NPD6535	Approved
0.765	Intermediate Similarity	NPD6534	Approved
0.7647	Intermediate Similarity	NPD6823	Phase 2
0.7643	Intermediate Similarity	NPD1933	Approved
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7240	Approved
0.7622	Intermediate Similarity	NPD7700	Phase 2
0.7622	Intermediate Similarity	NPD7699	Phase 2
0.7611	Intermediate Similarity	NPD8150	Discontinued
0.761	Intermediate Similarity	NPD7033	Discontinued
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1203	Approved
0.758	Intermediate Similarity	NPD1240	Approved
0.7577	Intermediate Similarity	NPD7930	Approved
0.7564	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1091	Approved
0.7548	Intermediate Similarity	NPD6832	Phase 2
0.7513	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD6213	Phase 3
0.75	Intermediate Similarity	NPD6212	Phase 3
0.75	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7584	Approved
0.7484	Intermediate Similarity	NPD1607	Approved
0.747	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5408	Approved
0.7453	Intermediate Similarity	NPD5406	Approved
0.7453	Intermediate Similarity	NPD5404	Approved
0.7453	Intermediate Similarity	NPD5405	Approved
0.7452	Intermediate Similarity	NPD6798	Discontinued
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7439	Intermediate Similarity	NPD6190	Approved
0.7423	Intermediate Similarity	NPD6674	Discontinued
0.7421	Intermediate Similarity	NPD447	Suspended
0.7421	Intermediate Similarity	NPD6355	Discontinued
0.7421	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD1608	Approved
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7358	Intermediate Similarity	NPD7585	Approved
0.7355	Intermediate Similarity	NPD2797	Approved
0.735	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3764	Approved
0.7342	Intermediate Similarity	NPD3268	Approved
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2798	Approved
0.7306	Intermediate Similarity	NPD7583	Approved
0.7301	Intermediate Similarity	NPD2344	Approved
0.7296	Intermediate Similarity	NPD6233	Phase 2
0.729	Intermediate Similarity	NPD3225	Approved
0.7287	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5953	Discontinued
0.7273	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2861	Phase 2
0.7246	Intermediate Similarity	NPD7390	Discontinued
0.7239	Intermediate Similarity	NPD6099	Approved
0.7239	Intermediate Similarity	NPD6100	Approved
0.7225	Intermediate Similarity	NPD4288	Approved
0.7222	Intermediate Similarity	NPD7097	Phase 1
0.7219	Intermediate Similarity	NPD920	Approved
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4908	Phase 1
0.7212	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2800	Approved
0.7211	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7177	Discontinued
0.7205	Intermediate Similarity	NPD230	Phase 1
0.7202	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD919	Approved
0.719	Intermediate Similarity	NPD17	Approved
0.7186	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7169	Intermediate Similarity	NPD7003	Approved
0.7167	Intermediate Similarity	NPD7286	Phase 2
0.7165	Intermediate Similarity	NPD7999	Approved
0.7158	Intermediate Similarity	NPD4420	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD943	Approved
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD2438	Suspended
0.7126	Intermediate Similarity	NPD2309	Approved
0.7125	Intermediate Similarity	NPD411	Approved
0.7125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6844	Discontinued

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