NPASS Compound

Structure

NPC93924 OpenBabel07101719122D 36 38 0 0 1 0 0 0 0 0999 V2000 8.6603 -8.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 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 2.5981 -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 9.5263 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 0 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 6.9282 -6.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 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 7.7942 -6.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 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 10.3923 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 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 7.7942 -7.5000 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 6.0622 -4.5000 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 32 1 0 0 0 0 2 33 1 0 0 0 0 3 7 2 0 0 0 0 3 14 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 26 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 27 1 0 0 0 0 15 18 2 0 0 0 0 16 34 1 0 0 0 0 17 19 2 0 0 0 0 17 35 1 0 0 0 0 18 32 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 28 2 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 31 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:	506.18
Volume:	490.888
LogP:	1.077
LogD:	1.324
LogS:	-3.984
# Rotatable Bonds:	11
TPSA:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	3.799
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.766
MDCK Permeability:	3.3632091799518093e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.561
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	81.65026092529297%
Volume Distribution (VD):	0.34
Pgp-substrate:	9.754837036132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.398
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.773
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	5.941
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.252
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.907
Carcinogencity:	0.587
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC93924

Natural Product ID:	NPC93924
*Common Name:**	Shomaside E
IUPAC Name:	[4-(2-hydroxyethyl)-3-methoxyphenyl] (E)-3-[3-methoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
Synonyms:	Shomaside E
Standard InCHIKey:	IFIROPVBDHQJPB-BIZNYIQVSA-N
Standard InCHI:	InChI=1S/C25H30O11/c1-32-18-12-16(6-5-15(18)9-10-26)34-21(28)8-4-14-3-7-17(19(11-14)33-2)35-25-24(31)23(30)22(29)20(13-27)36-25/h3-8,11-12,20,22-27,29-31H,9-10,13H2,1-2H3/b8-4+/t20-,22+,23+,24-,25-/m1/s1
SMILES:	OCCc1ccc(cc1OC)OC(=O)/C=C/c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096246
PubChem CID:	46210035
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
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO32999	cimicifuga heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	790000.0	nM	PMID[469700]

☑ 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 NPC93924 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	336
0.1-0.2	1540
0.2-0.3	3947
0.3-0.4	9366
0.4-0.5	8893
0.5-0.6	4434
0.6-0.7	6487
0.7-0.8	6264
0.8-0.85	1143
0.85-0.9	254
0.9-0.95	31
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC215060
0.9722	High Similarity	NPC476352
0.958	High Similarity	NPC96294
0.9521	High Similarity	NPC150442
0.9514	High Similarity	NPC106138
0.951	High Similarity	NPC52740
0.9452	High Similarity	NPC169404
0.9452	High Similarity	NPC176186
0.9452	High Similarity	NPC53587
0.9448	High Similarity	NPC114740
0.9441	High Similarity	NPC199928
0.9384	High Similarity	NPC213197
0.9375	High Similarity	NPC41844
0.9375	High Similarity	NPC15577
0.9329	High Similarity	NPC284810
0.932	High Similarity	NPC470264
0.931	High Similarity	NPC478237
0.931	High Similarity	NPC187398
0.931	High Similarity	NPC476348
0.9301	High Similarity	NPC292443
0.9301	High Similarity	NPC232228
0.9247	High Similarity	NPC206264
0.9247	High Similarity	NPC313334
0.9247	High Similarity	NPC212670
0.9241	High Similarity	NPC476347
0.9231	High Similarity	NPC478239
0.9189	High Similarity	NPC302610
0.9184	High Similarity	NPC21184
0.9184	High Similarity	NPC294522
0.9184	High Similarity	NPC205727
0.9184	High Similarity	NPC120426
0.9161	High Similarity	NPC157816
0.9161	High Similarity	NPC140502
0.9161	High Similarity	NPC475084
0.9155	High Similarity	NPC210478
0.9116	High Similarity	NPC176903
0.9116	High Similarity	NPC30688
0.9103	High Similarity	NPC475096
0.9103	High Similarity	NPC85624
0.9103	High Similarity	NPC226722
0.9091	High Similarity	NPC186406
0.9079	High Similarity	NPC241600
0.9079	High Similarity	NPC173726
0.9078	High Similarity	NPC103409
0.9078	High Similarity	NPC37468
0.9041	High Similarity	NPC190714
0.9041	High Similarity	NPC99515
0.9041	High Similarity	NPC125755
0.9028	High Similarity	NPC469559
0.9028	High Similarity	NPC145319
0.9028	High Similarity	NPC189115
0.9014	High Similarity	NPC124149
0.9007	High Similarity	NPC311430
0.9007	High Similarity	NPC224941
0.9	High Similarity	NPC215833
0.9	High Similarity	NPC69513
0.8986	High Similarity	NPC90896
0.8986	High Similarity	NPC283839
0.898	High Similarity	NPC87950
0.898	High Similarity	NPC227902
0.898	High Similarity	NPC296377
0.898	High Similarity	NPC471764
0.8973	High Similarity	NPC476450
0.8973	High Similarity	NPC100998
0.8973	High Similarity	NPC34587
0.8973	High Similarity	NPC476382
0.8973	High Similarity	NPC277867
0.8973	High Similarity	NPC161700
0.8973	High Similarity	NPC34927
0.8973	High Similarity	NPC252292
0.8966	High Similarity	NPC252169
0.8958	High Similarity	NPC469661
0.8958	High Similarity	NPC300611
0.8958	High Similarity	NPC215512
0.8958	High Similarity	NPC476442
0.8951	High Similarity	NPC100389
0.8951	High Similarity	NPC212770
0.8951	High Similarity	NPC98777
0.8944	High Similarity	NPC166180
0.8944	High Similarity	NPC471719
0.8936	High Similarity	NPC13745
0.8936	High Similarity	NPC251981
0.8936	High Similarity	NPC48863
0.8936	High Similarity	NPC187194
0.8933	High Similarity	NPC163598
0.8933	High Similarity	NPC264875
0.8933	High Similarity	NPC120774
0.8929	High Similarity	NPC162093
0.8919	High Similarity	NPC169510
0.8919	High Similarity	NPC175976
0.8919	High Similarity	NPC270751
0.8912	High Similarity	NPC205361
0.8912	High Similarity	NPC268515
0.8912	High Similarity	NPC40222
0.8912	High Similarity	NPC476865
0.8904	High Similarity	NPC469313
0.8904	High Similarity	NPC297342
0.8904	High Similarity	NPC138227
0.8904	High Similarity	NPC168579
0.8904	High Similarity	NPC76176
0.8904	High Similarity	NPC473045
0.8904	High Similarity	NPC25292
0.8897	High Similarity	NPC278469
0.8897	High Similarity	NPC193722
0.8897	High Similarity	NPC473792
0.8897	High Similarity	NPC473873
0.8896	High Similarity	NPC239966
0.8896	High Similarity	NPC203020
0.8889	High Similarity	NPC202700
0.8881	High Similarity	NPC59324
0.8881	High Similarity	NPC126206
0.8881	High Similarity	NPC65530
0.8873	High Similarity	NPC470236
0.8873	High Similarity	NPC55040
0.8873	High Similarity	NPC185778
0.8865	High Similarity	NPC263064
0.8865	High Similarity	NPC49074
0.8859	High Similarity	NPC111785
0.8851	High Similarity	NPC15538
0.8851	High Similarity	NPC232992
0.8851	High Similarity	NPC473480
0.8844	High Similarity	NPC476869
0.8844	High Similarity	NPC476868
0.8844	High Similarity	NPC476866
0.8844	High Similarity	NPC476864
0.8836	High Similarity	NPC473044
0.8836	High Similarity	NPC37793
0.8836	High Similarity	NPC138212
0.8831	High Similarity	NPC160780
0.8831	High Similarity	NPC289811
0.8828	High Similarity	NPC224876
0.8828	High Similarity	NPC83375
0.8828	High Similarity	NPC210192
0.8824	High Similarity	NPC473323
0.8819	High Similarity	NPC43500
0.8819	High Similarity	NPC164148
0.8811	High Similarity	NPC471665
0.8811	High Similarity	NPC25695
0.8811	High Similarity	NPC242028
0.8811	High Similarity	NPC157554
0.8811	High Similarity	NPC172818
0.8811	High Similarity	NPC471664
0.8811	High Similarity	NPC164857
0.8811	High Similarity	NPC203230
0.8811	High Similarity	NPC186418
0.8811	High Similarity	NPC104167
0.8808	High Similarity	NPC472611
0.8808	High Similarity	NPC472612
0.8808	High Similarity	NPC289967
0.8803	High Similarity	NPC309744
0.8803	High Similarity	NPC476411
0.8797	High Similarity	NPC116745
0.8794	High Similarity	NPC299144
0.8794	High Similarity	NPC5423
0.8786	High Similarity	NPC472024
0.8786	High Similarity	NPC80600
0.8786	High Similarity	NPC476399
0.8776	High Similarity	NPC476867
0.8776	High Similarity	NPC110063
0.8766	High Similarity	NPC472860
0.8766	High Similarity	NPC1913
0.8759	High Similarity	NPC267291
0.875	High Similarity	NPC470413
0.875	High Similarity	NPC137813
0.875	High Similarity	NPC138738
0.8741	High Similarity	NPC61946
0.8733	High Similarity	NPC476398
0.8733	High Similarity	NPC259347
0.8733	High Similarity	NPC94871
0.8733	High Similarity	NPC475250
0.8733	High Similarity	NPC473427
0.8733	High Similarity	NPC306890
0.8733	High Similarity	NPC476386
0.8733	High Similarity	NPC470933
0.8733	High Similarity	NPC471062
0.8732	High Similarity	NPC294166
0.8732	High Similarity	NPC115022
0.8726	High Similarity	NPC121290
0.8725	High Similarity	NPC39657
0.8723	High Similarity	NPC469698
0.8723	High Similarity	NPC473412
0.8723	High Similarity	NPC9912
0.8718	High Similarity	NPC472859
0.8718	High Similarity	NPC25389
0.8718	High Similarity	NPC182045
0.8718	High Similarity	NPC311803
0.8716	High Similarity	NPC83743
0.8716	High Similarity	NPC287615
0.8716	High Similarity	NPC216819
0.8716	High Similarity	NPC262182
0.8714	High Similarity	NPC270849
0.8714	High Similarity	NPC26653
0.871	High Similarity	NPC478269
0.8707	High Similarity	NPC91492
0.8707	High Similarity	NPC34245
0.8707	High Similarity	NPC81638
0.8707	High Similarity	NPC256555
0.8707	High Similarity	NPC7439
0.8707	High Similarity	NPC110067
0.8701	High Similarity	NPC228357

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 NPC93924 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	870
0.2-0.3	1814
0.3-0.4	2796
0.4-0.5	1747
0.5-0.6	960
0.6-0.7	547
0.7-0.8	127
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9247	High Similarity	NPD1653	Approved
0.8562	High Similarity	NPD7266	Discontinued
0.8403	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1613	Approved
0.8395	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7199	Phase 2
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1652	Phase 2
0.8194	Intermediate Similarity	NPD3027	Phase 3
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8153	Intermediate Similarity	NPD37	Approved
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4965	Approved
0.8113	Intermediate Similarity	NPD4967	Phase 2
0.8113	Intermediate Similarity	NPD4966	Approved
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8056	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1934	Approved
0.8037	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6559	Discontinued
0.8014	Intermediate Similarity	NPD1091	Approved
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD7228	Approved
0.7961	Intermediate Similarity	NPD6674	Discontinued
0.7949	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD5124	Phase 1
0.7852	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7240	Approved
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2801	Approved
0.7764	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD8455	Phase 2
0.7764	Intermediate Similarity	NPD1465	Phase 2
0.7762	Intermediate Similarity	NPD422	Phase 1
0.7756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7075	Discontinued
0.7716	Intermediate Similarity	NPD5402	Approved
0.7687	Intermediate Similarity	NPD3018	Phase 2
0.7669	Intermediate Similarity	NPD3882	Suspended
0.7661	Intermediate Similarity	NPD7549	Discontinued
0.7654	Intermediate Similarity	NPD7819	Suspended
0.7644	Intermediate Similarity	NPD6842	Approved
0.7644	Intermediate Similarity	NPD6841	Approved
0.7644	Intermediate Similarity	NPD6843	Phase 3
0.7643	Intermediate Similarity	NPD6799	Approved
0.7635	Intermediate Similarity	NPD4908	Phase 1
0.7616	Intermediate Similarity	NPD1933	Approved
0.761	Intermediate Similarity	NPD5403	Approved
0.7602	Intermediate Similarity	NPD7685	Pre-registration
0.7595	Intermediate Similarity	NPD5401	Approved
0.7593	Intermediate Similarity	NPD6801	Discontinued
0.7578	Intermediate Similarity	NPD4380	Phase 2
0.7547	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.7533	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1511	Approved
0.753	Intermediate Similarity	NPD5494	Approved
0.7517	Intermediate Similarity	NPD3705	Approved
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.744	Intermediate Similarity	NPD3787	Discontinued
0.744	Intermediate Similarity	NPD6232	Discontinued
0.7438	Intermediate Similarity	NPD1512	Approved
0.7434	Intermediate Similarity	NPD4060	Phase 1
0.7429	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7411	Suspended
0.7417	Intermediate Similarity	NPD6798	Discontinued
0.7415	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7097	Phase 1
0.7389	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.7362	Intermediate Similarity	NPD6599	Discontinued
0.7358	Intermediate Similarity	NPD5058	Phase 3
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7329	Intermediate Similarity	NPD3496	Discontinued
0.7325	Intermediate Similarity	NPD1549	Phase 2
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.731	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD1357	Approved
0.7308	Intermediate Similarity	NPD2796	Approved
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.7273	Intermediate Similarity	NPD4340	Discontinued
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7262	Intermediate Similarity	NPD919	Approved
0.7261	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5763	Approved
0.7261	Intermediate Similarity	NPD5762	Approved
0.7248	Intermediate Similarity	NPD3225	Approved
0.7244	Intermediate Similarity	NPD3748	Approved
0.7239	Intermediate Similarity	NPD3686	Approved
0.7239	Intermediate Similarity	NPD3687	Approved
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7237	Intermediate Similarity	NPD7095	Approved
0.7233	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7212	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4357	Discontinued
0.72	Intermediate Similarity	NPD2797	Approved
0.7197	Intermediate Similarity	NPD1551	Phase 2
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5535	Approved
0.7181	Intermediate Similarity	NPD4749	Approved
0.7179	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4538	Approved
0.7179	Intermediate Similarity	NPD4536	Approved
0.7174	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.717	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7125	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4110	Phase 3
0.7112	Intermediate Similarity	NPD7680	Approved
0.7102	Intermediate Similarity	NPD7039	Approved
0.7102	Intermediate Similarity	NPD7038	Approved
0.7097	Intermediate Similarity	NPD4140	Approved
0.709	Intermediate Similarity	NPD7583	Approved
0.7089	Intermediate Similarity	NPD2935	Discontinued
0.7089	Intermediate Similarity	NPD6032	Approved
0.7089	Intermediate Similarity	NPD3539	Phase 1
0.7083	Intermediate Similarity	NPD5353	Approved
0.7083	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD1358	Approved
0.7071	Intermediate Similarity	NPD290	Approved
0.707	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7843	Approved
0.7053	Intermediate Similarity	NPD7585	Approved
0.7052	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4678	Approved
0.7048	Intermediate Similarity	NPD4675	Approved
0.7034	Intermediate Similarity	NPD7157	Approved
0.7032	Intermediate Similarity	NPD4062	Phase 3
0.7027	Intermediate Similarity	NPD1778	Approved
0.7025	Intermediate Similarity	NPD5960	Phase 3
0.7025	Intermediate Similarity	NPD1510	Phase 2
0.7025	Intermediate Similarity	NPD5588	Approved
0.7021	Intermediate Similarity	NPD2684	Approved
0.702	Intermediate Similarity	NPD8651	Approved
0.7018	Intermediate Similarity	NPD5677	Discontinued
0.7006	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6971	Discontinued
0.6994	Remote Similarity	NPD3926	Phase 2
0.6994	Remote Similarity	NPD5242	Approved
0.6993	Remote Similarity	NPD228	Approved
0.6988	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6959	Discontinued
0.6975	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2677	Approved
0.6968	Remote Similarity	NPD1296	Phase 2
0.6959	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD5177	Phase 3
0.6951	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1375	Discontinued
0.6936	Remote Similarity	NPD7229	Phase 3
0.6927	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD2978	Approved
0.6923	Remote Similarity	NPD2977	Approved
0.6918	Remote Similarity	NPD4308	Phase 3

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