NPASS Compound

Structure

NPC145319 OpenBabel07101718312D 32 34 0 0 1 0 0 0 0 0999 V2000 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 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 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 6.0000 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 -1.7321 -0.0000 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 0.8660 -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 -6.0622 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 -7.7942 5.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 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 -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 4 1 0 0 0 0 1 12 2 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 8 2 0 0 0 0 3 12 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 30 1 0 0 0 0 13 16 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 18 26 2 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 31 1 1 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.14
Volume:	430.209
LogP:	1.092
LogD:	1.241
LogS:	-2.022
# Rotatable Bonds:	8
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	3.741
Fsp3:	0.318
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:	-6.306
MDCK Permeability:	9.142998351308051e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.167
Human Intestinal Absorption (HIA):	0.209
20% Bioavailability (F20%):	0.283
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	94.28780364990234%
Volume Distribution (VD):	0.363
Pgp-substrate:	4.411561012268066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.259
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.168
CYP2D6-substrate:	0.445
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	4.861
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.548
Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.947
Carcinogencity:	0.307
Eye Corrosion:	0.003
Eye Irritation:	0.07
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC145319

Natural Product ID:	NPC145319
*Common Name:**	Populoside A
IUPAC Name:	[5-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	KFXQFMPBHLWREX-KJXTXGEBSA-N
Standard InCHI:	InChI=1S/C22H24O10/c23-10-17-19(27)20(28)21(29)22(32-17)31-16-7-6-15(25)9-13(16)11-30-18(26)8-3-12-1-4-14(24)5-2-12/h1-9,17,19-25,27-29H,10-11H2/b8-3+/t17-,19-,20+,21-,22-/m1/s1
SMILES:	c1cc(ccc1/C=C/C(=O)OCc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465420
PubChem CID:	16086606
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
NPO14695	Populus davidiana	Species	Salicaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[16989539]
NPO14695	Populus davidiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14695	Populus davidiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14695	Populus davidiana	Species	Salicaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Activity	=	2.07	n.a.	PMID[483343]

☑ 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 NPC145319 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	340
0.1-0.2	1509
0.2-0.3	4054
0.3-0.4	9182
0.4-0.5	8959
0.5-0.6	4470
0.6-0.7	7909
0.7-0.8	5525
0.8-0.85	617
0.85-0.9	108
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9627	High Similarity	NPC166180
0.9565	High Similarity	NPC292443
0.9429	High Similarity	NPC199928
0.9424	High Similarity	NPC232228
0.9357	High Similarity	NPC138915
0.9348	High Similarity	NPC186406
0.9296	High Similarity	NPC4958
0.9296	High Similarity	NPC92054
0.9296	High Similarity	NPC140722
0.9214	High Similarity	NPC478239
0.9161	High Similarity	NPC478237
0.9143	High Similarity	NPC157816
0.913	High Similarity	NPC124149
0.9103	High Similarity	NPC213197
0.9103	High Similarity	NPC93619
0.9097	High Similarity	NPC313334
0.9097	High Similarity	NPC206264
0.9097	High Similarity	NPC212670
0.903	High Similarity	NPC40377
0.903	High Similarity	NPC146540
0.9028	High Similarity	NPC96294
0.9028	High Similarity	NPC93924
0.9014	High Similarity	NPC476867
0.9007	High Similarity	NPC140502
0.9	High Similarity	NPC202700
0.8986	High Similarity	NPC185778
0.8966	High Similarity	NPC106138
0.8958	High Similarity	NPC41844
0.8951	High Similarity	NPC476869
0.8951	High Similarity	NPC476864
0.8951	High Similarity	NPC476868
0.8951	High Similarity	NPC476866
0.8951	High Similarity	NPC226722
0.8944	High Similarity	NPC252169
0.8929	High Similarity	NPC100389
0.8921	High Similarity	NPC103409
0.8921	High Similarity	NPC37468
0.8921	High Similarity	NPC186418
0.8919	High Similarity	NPC230439
0.8919	High Similarity	NPC92153
0.8919	High Similarity	NPC279281
0.8919	High Similarity	NPC299761
0.8912	High Similarity	NPC169404
0.8912	High Similarity	NPC176186
0.8912	High Similarity	NPC53587
0.8905	High Similarity	NPC85799
0.8905	High Similarity	NPC303422
0.8905	High Similarity	NPC26080
0.8905	High Similarity	NPC165686
0.8904	High Similarity	NPC114740
0.8889	High Similarity	NPC476865
0.8873	High Similarity	NPC245219
0.8873	High Similarity	NPC65833
0.8873	High Similarity	NPC31081
0.8851	High Similarity	NPC215811
0.8851	High Similarity	NPC150442
0.8841	High Similarity	NPC294166
0.8841	High Similarity	NPC115022
0.8832	High Similarity	NPC121376
0.8828	High Similarity	NPC52740
0.8824	High Similarity	NPC97326
0.8824	High Similarity	NPC295970
0.8819	High Similarity	NPC252292
0.8819	High Similarity	NPC34927
0.8819	High Similarity	NPC100998
0.8819	High Similarity	NPC34587
0.8819	High Similarity	NPC476382
0.8815	High Similarity	NPC288416
0.8803	High Similarity	NPC476442
0.8803	High Similarity	NPC215512
0.8803	High Similarity	NPC210192
0.88	High Similarity	NPC284810
0.8792	High Similarity	NPC299435
0.8792	High Similarity	NPC185103
0.8792	High Similarity	NPC260604
0.8786	High Similarity	NPC471664
0.8786	High Similarity	NPC157554
0.8786	High Similarity	NPC471665
0.8784	High Similarity	NPC476352
0.8784	High Similarity	NPC215060
0.8777	High Similarity	NPC886
0.8777	High Similarity	NPC287597
0.8777	High Similarity	NPC188555
0.8777	High Similarity	NPC130496
0.8777	High Similarity	NPC34293
0.8776	High Similarity	NPC120426
0.8776	High Similarity	NPC294522
0.8776	High Similarity	NPC205727
0.8776	High Similarity	NPC21184
0.8767	High Similarity	NPC83975
0.875	High Similarity	NPC110063
0.8742	High Similarity	NPC474398
0.8742	High Similarity	NPC474441
0.8742	High Similarity	NPC474401
0.8742	High Similarity	NPC476026
0.8741	High Similarity	NPC475084
0.8723	High Similarity	NPC126206
0.8723	High Similarity	NPC78363
0.8714	High Similarity	NPC476870
0.8714	High Similarity	NPC238243
0.8714	High Similarity	NPC79957
0.8707	High Similarity	NPC30688
0.8707	High Similarity	NPC176903
0.8707	High Similarity	NPC111785
0.8699	High Similarity	NPC15577
0.8699	High Similarity	NPC474422
0.8699	High Similarity	NPC227902
0.8699	High Similarity	NPC232992
0.8696	High Similarity	NPC246869
0.8696	High Similarity	NPC138777
0.8696	High Similarity	NPC225384
0.869	High Similarity	NPC216819
0.869	High Similarity	NPC85624
0.869	High Similarity	NPC83743
0.869	High Similarity	NPC262182
0.869	High Similarity	NPC287615
0.8686	High Similarity	NPC218003
0.8684	High Similarity	NPC57072
0.8684	High Similarity	NPC287872
0.8684	High Similarity	NPC74319
0.8684	High Similarity	NPC231475
0.8667	High Similarity	NPC126991
0.8667	High Similarity	NPC83218
0.8662	High Similarity	NPC226005
0.8652	High Similarity	NPC242028
0.8652	High Similarity	NPC40664
0.8652	High Similarity	NPC3293
0.8652	High Similarity	NPC203230
0.8652	High Similarity	NPC165482
0.8652	High Similarity	NPC138350
0.8652	High Similarity	NPC197723
0.8649	High Similarity	NPC476871
0.8649	High Similarity	NPC100818
0.8649	High Similarity	NPC182350
0.8643	High Similarity	NPC87696
0.8639	High Similarity	NPC187398
0.8639	High Similarity	NPC476348
0.8639	High Similarity	NPC169510
0.8639	High Similarity	NPC175976
0.863	High Similarity	NPC74320
0.863	High Similarity	NPC107120
0.863	High Similarity	NPC268515
0.863	High Similarity	NPC40222
0.8621	High Similarity	NPC76176
0.8621	High Similarity	NPC138227
0.8621	High Similarity	NPC469313
0.8621	High Similarity	NPC168579
0.8613	High Similarity	NPC225307
0.8611	High Similarity	NPC164599
0.8603	High Similarity	NPC471157
0.86	High Similarity	NPC183536
0.86	High Similarity	NPC34965
0.8592	High Similarity	NPC59324
0.8592	High Similarity	NPC134260
0.8592	High Similarity	NPC262328
0.8592	High Similarity	NPC138738
0.8592	High Similarity	NPC470413
0.8592	High Similarity	NPC65530
0.8592	High Similarity	NPC260425
0.8592	High Similarity	NPC87777
0.8582	High Similarity	NPC55040
0.8582	High Similarity	NPC52097
0.8581	High Similarity	NPC306890
0.8581	High Similarity	NPC94871
0.8581	High Similarity	NPC476386
0.8581	High Similarity	NPC471062
0.8581	High Similarity	NPC473427
0.8581	High Similarity	NPC259347
0.8581	High Similarity	NPC90896
0.8581	High Similarity	NPC476398
0.8581	High Similarity	NPC283839
0.8581	High Similarity	NPC470933
0.8571	High Similarity	NPC471764
0.8571	High Similarity	NPC472859
0.8571	High Similarity	NPC311803
0.8571	High Similarity	NPC476347
0.8571	High Similarity	NPC25389
0.8571	High Similarity	NPC87950
0.8571	High Similarity	NPC97240
0.8571	High Similarity	NPC296377
0.8562	High Similarity	NPC478269
0.8562	High Similarity	NPC475096
0.8561	High Similarity	NPC235294
0.8561	High Similarity	NPC46137
0.8561	High Similarity	NPC166168
0.8561	High Similarity	NPC478255
0.8553	High Similarity	NPC228357
0.8552	High Similarity	NPC37793
0.8551	High Similarity	NPC229784
0.8551	High Similarity	NPC477294
0.8551	High Similarity	NPC477293
0.8543	High Similarity	NPC327032
0.8543	High Similarity	NPC191046
0.8543	High Similarity	NPC194095
0.8542	High Similarity	NPC469661
0.8542	High Similarity	NPC134405
0.8542	High Similarity	NPC476385
0.854	High Similarity	NPC140750
0.8533	High Similarity	NPC163598
0.8533	High Similarity	NPC36130

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 NPC145319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	839
0.2-0.3	1829
0.3-0.4	2749
0.4-0.5	1768
0.5-0.6	1011
0.6-0.7	554
0.7-0.8	113
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD1653	Approved
0.8531	High Similarity	NPD7266	Discontinued
0.8507	High Similarity	NPD1091	Approved
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2861	Phase 2
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD3818	Discontinued
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD8455	Phase 2
0.7914	Intermediate Similarity	NPD7054	Approved
0.7898	Intermediate Similarity	NPD5402	Approved
0.7866	Intermediate Similarity	NPD7472	Approved
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.78	Intermediate Similarity	NPD1652	Phase 2
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD3496	Discontinued
0.7762	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD4060	Phase 1
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7697	Intermediate Similarity	NPD6190	Approved
0.7697	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7075	Discontinued
0.7679	Intermediate Similarity	NPD8312	Approved
0.7679	Intermediate Similarity	NPD8313	Approved
0.7671	Intermediate Similarity	NPD6233	Phase 2
0.7655	Intermediate Similarity	NPD3027	Phase 3
0.7643	Intermediate Similarity	NPD4380	Phase 2
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7586	Intermediate Similarity	NPD4908	Phase 1
0.7572	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5124	Phase 1
0.7568	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4340	Discontinued
0.7566	Intermediate Similarity	NPD6674	Discontinued
0.7564	Intermediate Similarity	NPD5403	Approved
0.756	Intermediate Similarity	NPD7685	Pre-registration
0.7554	Intermediate Similarity	NPD1548	Phase 1
0.7552	Intermediate Similarity	NPD3225	Approved
0.7547	Intermediate Similarity	NPD37	Approved
0.7547	Intermediate Similarity	NPD1934	Approved
0.7546	Intermediate Similarity	NPD7199	Phase 2
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD3751	Discontinued
0.753	Intermediate Similarity	NPD7228	Approved
0.7516	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7097	Phase 1
0.7467	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3817	Phase 2
0.7451	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6801	Discontinued
0.7436	Intermediate Similarity	NPD5401	Approved
0.7436	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5058	Phase 3
0.741	Intermediate Similarity	NPD6166	Phase 2
0.741	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3750	Approved
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7391	Intermediate Similarity	NPD7819	Suspended
0.7386	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD6799	Approved
0.7368	Intermediate Similarity	NPD1551	Phase 2
0.7361	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6671	Approved
0.7338	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD1933	Approved
0.732	Intermediate Similarity	NPD5762	Approved
0.732	Intermediate Similarity	NPD5763	Approved
0.732	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD968	Approved
0.7303	Intermediate Similarity	NPD7033	Discontinued
0.7297	Intermediate Similarity	NPD7095	Approved
0.729	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1465	Phase 2
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7261	Intermediate Similarity	NPD1511	Approved
0.726	Intermediate Similarity	NPD1203	Approved
0.726	Intermediate Similarity	NPD2797	Approved
0.7259	Intermediate Similarity	NPD1358	Approved
0.7259	Intermediate Similarity	NPD290	Approved
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4536	Approved
0.7237	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4538	Approved
0.7233	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7209	Intermediate Similarity	NPD7549	Discontinued
0.7203	Intermediate Similarity	NPD1778	Approved
0.7195	Intermediate Similarity	NPD3882	Suspended
0.719	Intermediate Similarity	NPD5588	Approved
0.719	Intermediate Similarity	NPD5960	Phase 3
0.7181	Intermediate Similarity	NPD4625	Phase 3
0.7179	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1481	Phase 2
0.7171	Intermediate Similarity	NPD6653	Approved
0.717	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1512	Approved
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7133	Intermediate Similarity	NPD1357	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4749	Approved
0.7122	Intermediate Similarity	NPD5535	Approved
0.7122	Intermediate Similarity	NPD7843	Approved
0.7114	Intermediate Similarity	NPD6832	Phase 2
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD447	Suspended
0.7103	Intermediate Similarity	NPD3705	Approved
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7092	Intermediate Similarity	NPD7157	Approved
0.7091	Intermediate Similarity	NPD7768	Phase 2
0.7088	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD6781	Approved
0.7088	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD6779	Approved
0.7088	Intermediate Similarity	NPD6782	Approved
0.7088	Intermediate Similarity	NPD6780	Approved
0.7086	Intermediate Similarity	NPD4062	Phase 3
0.7083	Intermediate Similarity	NPD4626	Approved
0.708	Intermediate Similarity	NPD2684	Approved
0.7078	Intermediate Similarity	NPD1510	Phase 2
0.7078	Intermediate Similarity	NPD3748	Approved
0.7075	Intermediate Similarity	NPD8651	Approved
0.7074	Intermediate Similarity	NPD7783	Phase 2
0.7074	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5494	Approved
0.7059	Intermediate Similarity	NPD3134	Approved
0.7055	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3018	Phase 2
0.7039	Intermediate Similarity	NPD4140	Approved
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD2796	Approved
0.703	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8127	Discontinued
0.7014	Intermediate Similarity	NPD5691	Approved
0.7014	Intermediate Similarity	NPD5585	Approved
0.7011	Intermediate Similarity	NPD6823	Phase 2
0.7006	Intermediate Similarity	NPD6841	Approved
0.7006	Intermediate Similarity	NPD6843	Phase 3
0.7006	Intermediate Similarity	NPD6842	Approved
0.7	Intermediate Similarity	NPD3536	Discontinued
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD230	Phase 1
0.6993	Remote Similarity	NPD5536	Phase 2
0.6986	Remote Similarity	NPD1611	Approved
0.6985	Remote Similarity	NPD9697	Approved
0.6982	Remote Similarity	NPD6232	Discontinued
0.6968	Remote Similarity	NPD4308	Phase 3
0.6966	Remote Similarity	NPD6516	Phase 2
0.6966	Remote Similarity	NPD5846	Approved
0.6964	Remote Similarity	NPD4666	Phase 3
0.6962	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1894	Discontinued
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9717	Approved
0.6939	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD3226	Approved
0.6931	Remote Similarity	NPD7874	Approved
0.6931	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD969	Suspended
0.6923	Remote Similarity	NPD6959	Discontinued
0.6918	Remote Similarity	NPD2677	Approved
0.6915	Remote Similarity	NPD7585	Approved
0.6909	Remote Similarity	NPD4433	Discontinued
0.6908	Remote Similarity	NPD1048	Approved
0.6908	Remote Similarity	NPD2313	Discontinued
0.6905	Remote Similarity	NPD5709	Phase 3
0.6894	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2983	Phase 2
0.6892	Remote Similarity	NPD2982	Phase 2

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