NPASS Compound

Structure

NPC304894 OpenBabel07101719512D 36 40 0 0 1 0 0 0 0 0999 V2000 -4.2072 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7614 2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0933 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4087 3.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4305 3.2464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7177 2.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0933 3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1215 4.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6958 1.8795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 1.3309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 4.3776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 2.3309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5933 2.6456 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 3 2 0 0 0 0 1 14 1 0 0 0 0 2 5 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 6 2 0 0 0 0 4 16 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 14 2 0 0 0 0 7 23 1 0 0 0 0 8 15 2 0 0 0 0 8 20 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 19 2 0 0 0 0 11 16 2 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 25 1 0 0 0 0 15 26 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 23 2 0 0 0 0 21 32 1 0 0 0 0 22 24 2 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 26 2 0 0 0 0 25 36 1 0 0 0 0 26 27 1 0 0 0 0 27 17 1 6 0 0 0 27 28 1 0 0 0 0 28 16 1 1 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.13
Volume:	486.11
LogP:	3.955
LogD:	3.199
LogS:	-3.746
# Rotatable Bonds:	4
TPSA:	150.84
# H-Bond Aceptor:	8
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	3.743
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.956
MDCK Permeability:	8.015131243155338e-06
Pgp-inhibitor:	0.357
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.092
20% Bioavailability (F20%):	0.436
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	94.38272857666016%
Volume Distribution (VD):	0.587
Pgp-substrate:	3.5931508541107178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.793
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	18.816
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.364
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.976
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.935
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC304894

Natural Product ID:	NPC304894
*Common Name:**	Trans-Scirpusin B
IUPAC Name:	4-[(E)-2-[(2S,3S)-2-(3,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-1-benzofuran-4-yl]ethenyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	MTYSFTYBAMMIGE-MJECPWISSA-N
Standard InCHI:	InChI=1S/C28H22O8/c29-18-9-17(10-19(30)12-18)27-26-15(3-1-14-2-5-21(32)23(34)7-14)8-20(31)13-25(26)36-28(27)16-4-6-22(33)24(35)11-16/h1-13,27-35H/b3-1+/t27-,28+/m0/s1
SMILES:	C(=Cc1cc(cc2c1[C@H](c1cc(cc(c1)O)O)[C@@H](c1ccc(c(c1)O)O)O2)O)/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL596359
PubChem CID:	21633205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	2.2	n.a.	PMID[529847]

☑ 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 NPC304894 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	517
0.1-0.2	1713
0.2-0.3	4662
0.3-0.4	11978
0.4-0.5	6073
0.5-0.6	4148
0.6-0.7	6879
0.7-0.8	5297
0.8-0.85	870
0.85-0.9	456
0.9-0.95	96
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC15659
0.9926	High Similarity	NPC173203
0.9926	High Similarity	NPC163508
0.9574	High Similarity	NPC329836
0.9437	High Similarity	NPC227516
0.9437	High Similarity	NPC20757
0.9412	High Similarity	NPC11727
0.9412	High Similarity	NPC15109
0.9353	High Similarity	NPC178054
0.9315	High Similarity	NPC157333
0.931	High Similarity	NPC476391
0.9281	High Similarity	NPC213607
0.9281	High Similarity	NPC22317
0.9281	High Similarity	NPC182509
0.9281	High Similarity	NPC174787
0.9241	High Similarity	NPC321972
0.9241	High Similarity	NPC329343
0.9241	High Similarity	NPC324517
0.9231	High Similarity	NPC170103
0.9231	High Similarity	NPC263940
0.9231	High Similarity	NPC262911
0.9231	High Similarity	NPC294558
0.9231	High Similarity	NPC18185
0.9231	High Similarity	NPC236202
0.9231	High Similarity	NPC70409
0.9231	High Similarity	NPC204770
0.9231	High Similarity	NPC108811
0.9231	High Similarity	NPC202742
0.9231	High Similarity	NPC58190
0.9231	High Similarity	NPC82917
0.9203	High Similarity	NPC234952
0.9203	High Similarity	NPC141717
0.9161	High Similarity	NPC324492
0.9161	High Similarity	NPC96576
0.9161	High Similarity	NPC317053
0.9161	High Similarity	NPC260397
0.9155	High Similarity	NPC28440
0.9155	High Similarity	NPC171932
0.9143	High Similarity	NPC184797
0.9143	High Similarity	NPC262189
0.9143	High Similarity	NPC309124
0.9137	High Similarity	NPC474390
0.913	High Similarity	NPC125579
0.9122	High Similarity	NPC202104
0.9103	High Similarity	NPC473266
0.9103	High Similarity	NPC318373
0.9103	High Similarity	NPC211561
0.9103	High Similarity	NPC470098
0.9103	High Similarity	NPC476969
0.9103	High Similarity	NPC470826
0.9103	High Similarity	NPC321657
0.9097	High Similarity	NPC320970
0.9097	High Similarity	NPC320671
0.9097	High Similarity	NPC328567
0.9097	High Similarity	NPC327412
0.9071	High Similarity	NPC55947
0.9071	High Similarity	NPC232164
0.9071	High Similarity	NPC473739
0.9071	High Similarity	NPC32630
0.9071	High Similarity	NPC236306
0.9058	High Similarity	NPC66840
0.9058	High Similarity	NPC256307
0.9041	High Similarity	NPC477612
0.9021	High Similarity	NPC473108
0.9021	High Similarity	NPC471415
0.9021	High Similarity	NPC470097
0.9021	High Similarity	NPC114119
0.9014	High Similarity	NPC107161
0.9014	High Similarity	NPC277784
0.9007	High Similarity	NPC160283
0.9007	High Similarity	NPC291101
0.9007	High Similarity	NPC472090
0.9007	High Similarity	NPC254759
0.9007	High Similarity	NPC266197
0.9007	High Similarity	NPC20520
0.9007	High Similarity	NPC61783
0.9007	High Similarity	NPC472091
0.9007	High Similarity	NPC472092
0.9	High Similarity	NPC94994
0.8986	High Similarity	NPC11060
0.8958	High Similarity	NPC149633
0.8958	High Similarity	NPC181615
0.8951	High Similarity	NPC469630
0.8944	High Similarity	NPC87725
0.8944	High Similarity	NPC247291
0.8944	High Similarity	NPC311530
0.8944	High Similarity	NPC265075
0.8944	High Similarity	NPC263261
0.8944	High Similarity	NPC470372
0.8936	High Similarity	NPC292882
0.8936	High Similarity	NPC22517
0.8929	High Similarity	NPC265433
0.8929	High Similarity	NPC270456
0.8929	High Similarity	NPC248727
0.8929	High Similarity	NPC162659
0.8919	High Similarity	NPC279406
0.8919	High Similarity	NPC44192
0.8919	High Similarity	NPC226108
0.8919	High Similarity	NPC469944
0.8919	High Similarity	NPC226809
0.8919	High Similarity	NPC322899
0.8919	High Similarity	NPC272552
0.8919	High Similarity	NPC134911
0.8919	High Similarity	NPC233467
0.8919	High Similarity	NPC46283
0.8913	High Similarity	NPC474134
0.8913	High Similarity	NPC131128
0.8904	High Similarity	NPC281549
0.8897	High Similarity	NPC176804
0.8897	High Similarity	NPC71686
0.8889	High Similarity	NPC45257
0.8889	High Similarity	NPC93323
0.8889	High Similarity	NPC280092
0.8889	High Similarity	NPC12641
0.8881	High Similarity	NPC472088
0.8881	High Similarity	NPC472087
0.8874	High Similarity	NPC470827
0.8874	High Similarity	NPC125495
0.8873	High Similarity	NPC55793
0.8873	High Similarity	NPC27495
0.8865	High Similarity	NPC48956
0.8865	High Similarity	NPC211549
0.8859	High Similarity	NPC306267
0.8859	High Similarity	NPC20050
0.8859	High Similarity	NPC224161
0.8857	High Similarity	NPC470356
0.8857	High Similarity	NPC121812
0.8857	High Similarity	NPC112246
0.8857	High Similarity	NPC474206
0.8857	High Similarity	NPC473413
0.8857	High Similarity	NPC112939
0.8857	High Similarity	NPC94750
0.8857	High Similarity	NPC151224
0.8857	High Similarity	NPC164787
0.8849	High Similarity	NPC158331
0.8836	High Similarity	NPC16269
0.8836	High Similarity	NPC133209
0.8836	High Similarity	NPC237546
0.8836	High Similarity	NPC6702
0.8836	High Similarity	NPC224921
0.8836	High Similarity	NPC112819
0.8836	High Similarity	NPC231712
0.8836	High Similarity	NPC242774
0.8836	High Similarity	NPC111134
0.8836	High Similarity	NPC21776
0.8832	High Similarity	NPC471518
0.8832	High Similarity	NPC471519
0.8819	High Similarity	NPC102044
0.8819	High Similarity	NPC155392
0.8819	High Similarity	NPC47633
0.8819	High Similarity	NPC135767
0.8819	High Similarity	NPC274721
0.8819	High Similarity	NPC85264
0.8819	High Similarity	NPC477616
0.8816	High Similarity	NPC470828
0.8811	High Similarity	NPC100482
0.8811	High Similarity	NPC277331
0.8811	High Similarity	NPC472089
0.8811	High Similarity	NPC471389
0.8803	High Similarity	NPC184613
0.8803	High Similarity	NPC260842
0.8803	High Similarity	NPC245207
0.8803	High Similarity	NPC6300
0.8803	High Similarity	NPC230124
0.8803	High Similarity	NPC319647
0.8803	High Similarity	NPC127218
0.8803	High Similarity	NPC70682
0.8803	High Similarity	NPC114171
0.8803	High Similarity	NPC25966
0.8803	High Similarity	NPC260741
0.88	High Similarity	NPC46335
0.8794	High Similarity	NPC227503
0.8794	High Similarity	NPC16435
0.8794	High Similarity	NPC474639
0.8794	High Similarity	NPC269091
0.8794	High Similarity	NPC77861
0.8794	High Similarity	NPC230734
0.8794	High Similarity	NPC302701
0.8794	High Similarity	NPC306441
0.8792	High Similarity	NPC160196
0.8786	High Similarity	NPC317380
0.8786	High Similarity	NPC244983
0.8786	High Similarity	NPC326095
0.8786	High Similarity	NPC287745
0.8777	High Similarity	NPC15658
0.8777	High Similarity	NPC204215
0.8777	High Similarity	NPC126029
0.8777	High Similarity	NPC175067
0.8777	High Similarity	NPC261619
0.8777	High Similarity	NPC78770
0.8777	High Similarity	NPC61477
0.8777	High Similarity	NPC185604
0.8777	High Similarity	NPC219876
0.8767	High Similarity	NPC268515
0.8767	High Similarity	NPC233980
0.8767	High Similarity	NPC87794
0.8767	High Similarity	NPC211758
0.8767	High Similarity	NPC40222
0.8767	High Similarity	NPC14468
0.8767	High Similarity	NPC112251

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 NPC304894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	889
0.2-0.3	1885
0.3-0.4	2715
0.4-0.5	1605
0.5-0.6	919
0.6-0.7	581
0.7-0.8	121
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD1613	Approved
0.8777	High Similarity	NPD1612	Clinical (unspecified phase)
0.8623	High Similarity	NPD4908	Phase 1
0.8623	High Similarity	NPD1529	Clinical (unspecified phase)
0.8551	High Similarity	NPD1530	Clinical (unspecified phase)
0.85	High Similarity	NPD4907	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3027	Phase 3
0.8248	Intermediate Similarity	NPD1610	Phase 2
0.8156	Intermediate Similarity	NPD2861	Phase 2
0.8101	Intermediate Similarity	NPD6234	Discontinued
0.8089	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7917	Intermediate Similarity	NPD4625	Phase 3
0.7901	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD37	Approved
0.7866	Intermediate Similarity	NPD7228	Approved
0.7862	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD4966	Approved
0.7853	Intermediate Similarity	NPD6166	Phase 2
0.7853	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1934	Approved
0.7746	Intermediate Similarity	NPD4749	Approved
0.7725	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6674	Discontinued
0.7669	Intermediate Similarity	NPD6959	Discontinued
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7643	Intermediate Similarity	NPD1653	Approved
0.7635	Intermediate Similarity	NPD3620	Phase 2
0.7635	Intermediate Similarity	NPD4060	Phase 1
0.7635	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1511	Approved
0.7605	Intermediate Similarity	NPD5844	Phase 1
0.7566	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8053	Approved
0.7544	Intermediate Similarity	NPD8054	Approved
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.7532	Intermediate Similarity	NPD3892	Phase 2
0.7531	Intermediate Similarity	NPD3882	Suspended
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD2801	Approved
0.7516	Intermediate Similarity	NPD7037	Approved
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD7212	Phase 2
0.7469	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5735	Approved
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7447	Phase 1
0.7419	Intermediate Similarity	NPD3750	Approved
0.7419	Intermediate Similarity	NPD7466	Approved
0.741	Intermediate Similarity	NPD6232	Discontinued
0.741	Intermediate Similarity	NPD7229	Phase 3
0.7396	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD5494	Approved
0.7384	Intermediate Similarity	NPD4577	Approved
0.7384	Intermediate Similarity	NPD4578	Approved
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7379	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2982	Phase 2
0.7379	Intermediate Similarity	NPD2983	Phase 2
0.7368	Intermediate Similarity	NPD7240	Approved
0.7361	Intermediate Similarity	NPD3705	Approved
0.7356	Intermediate Similarity	NPD4663	Approved
0.7353	Intermediate Similarity	NPD7472	Approved
0.7347	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5283	Phase 1
0.7329	Intermediate Similarity	NPD4380	Phase 2
0.7317	Intermediate Similarity	NPD7768	Phase 2
0.7314	Intermediate Similarity	NPD7906	Approved
0.731	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD2981	Phase 2
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD8455	Phase 2
0.7299	Intermediate Similarity	NPD3021	Approved
0.7299	Intermediate Similarity	NPD3022	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7251	Discontinued
0.726	Intermediate Similarity	NPD5327	Phase 3
0.7256	Intermediate Similarity	NPD3817	Phase 2
0.7241	Intermediate Similarity	NPD1091	Approved
0.7237	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6584	Phase 3
0.7226	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7266	Discontinued
0.7226	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD5763	Approved
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7549	Discontinued
0.7219	Intermediate Similarity	NPD27	Approved
0.7219	Intermediate Similarity	NPD2489	Approved
0.7211	Intermediate Similarity	NPD6696	Suspended
0.7208	Intermediate Similarity	NPD5588	Approved
0.7202	Intermediate Similarity	NPD3051	Approved
0.72	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7194	Intermediate Similarity	NPD228	Approved
0.7193	Intermediate Similarity	NPD8156	Discontinued
0.7184	Intermediate Similarity	NPD7313	Approved
0.7184	Intermediate Similarity	NPD7312	Approved
0.7184	Intermediate Similarity	NPD7311	Approved
0.7184	Intermediate Similarity	NPD7310	Approved
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7171	Intermediate Similarity	NPD4140	Approved
0.717	Intermediate Similarity	NPD7041	Phase 2
0.717	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD3094	Phase 2
0.716	Intermediate Similarity	NPD2969	Approved
0.716	Intermediate Similarity	NPD2970	Approved
0.716	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7309	Approved
0.7135	Intermediate Similarity	NPD8251	Approved
0.7135	Intermediate Similarity	NPD8099	Discontinued
0.7135	Intermediate Similarity	NPD8252	Approved
0.7126	Intermediate Similarity	NPD7808	Phase 3
0.7125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7118	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6671	Approved
0.7113	Intermediate Similarity	NPD7157	Approved
0.7103	Intermediate Similarity	NPD6516	Phase 2
0.7103	Intermediate Similarity	NPD5846	Approved
0.7097	Intermediate Similarity	NPD3748	Approved
0.7095	Intermediate Similarity	NPD8651	Approved
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7081	Intermediate Similarity	NPD7680	Approved
0.7081	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6353	Approved
0.7078	Intermediate Similarity	NPD4097	Suspended
0.7073	Intermediate Similarity	NPD7411	Suspended
0.7066	Intermediate Similarity	NPD7075	Discontinued
0.7066	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1558	Phase 1
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4005	Discontinued
0.7049	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2560	Approved
0.7048	Intermediate Similarity	NPD5402	Approved
0.7048	Intermediate Similarity	NPD2563	Approved
0.7045	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6190	Approved
0.7039	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3751	Discontinued
0.7032	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4536	Approved
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7032	Intermediate Similarity	NPD4538	Approved
0.7027	Intermediate Similarity	NPD6582	Phase 2
0.7027	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6583	Phase 3
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7021	Intermediate Similarity	NPD7843	Approved
0.7012	Intermediate Similarity	NPD4678	Approved
0.7012	Intermediate Similarity	NPD4675	Approved
0.7007	Intermediate Similarity	NPD3092	Approved
0.7006	Intermediate Similarity	NPD3540	Phase 1
0.7	Intermediate Similarity	NPD5058	Phase 3
0.6993	Remote Similarity	NPD6233	Phase 2
0.6987	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1510	Phase 2
0.6987	Remote Similarity	NPD5960	Phase 3
0.6981	Remote Similarity	NPD6331	Phase 2
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2684	Approved
0.6974	Remote Similarity	NPD7095	Approved
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7831	Phase 2
0.6964	Remote Similarity	NPD7833	Phase 2
0.6962	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1840	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