NPASS Compound

Structure

CID313081 OpenBabel06191716122D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 1.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 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 -1.5000 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 -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 -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 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 0.8660 1.5000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 1 1 1 0 0 0 11 12 1 0 0 0 0 12 2 1 1 0 0 0 12 18 1 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 13 1 6 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	374.235
LogP:	4.385
LogD:	4.07
LogS:	-4.225
# Rotatable Bonds:	4
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	3.526
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	1.5179559341049753e-05
Pgp-inhibitor:	0.305
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.367

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.55377197265625%
Volume Distribution (VD):	0.535
Pgp-substrate:	2.783848762512207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.595
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.259
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	7.352
Half-life (T1/2):	0.594

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.358
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.431
Skin Sensitization:	0.291
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.528
Respiratory Toxicity:	0.484

Download Data

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

Natural Product: NPC313081

Natural Product ID:	NPC313081
*Common Name:**	(-)-(7'r,8R,8'r)-4,4'-Dihydroxy-3,3',5-Trimethoxy-2,7'-Cyclolignane
IUPAC Name:	(6R,7R,8R)-8-(4-hydroxy-3-methoxyphenyl)-1,3-dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	VEFZLUCJNOJAGR-SEDUGSJDSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-11-8-14-10-17(25-4)20(23)21(26-5)19(14)18(12(11)2)13-6-7-15(22)16(9-13)24-3/h6-7,9-12,18,22-23H,8H2,1-5H3/t11-,12-,18-/m1/s1
SMILES:	C[C@@H]1Cc2cc(c(c(c2[C@H]([C@@H]1C)c1ccc(c(c1)OC)O)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079839
PubChem CID:	44613160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO23895	Machilus wangchiana	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[19916529]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23895	Machilus wangchiana	Species	Lauraceae	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.	Inhibition	=	47.0	%	PMID[510932]

☑ 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 NPC313081 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	452
0.1-0.2	1665
0.2-0.3	4238
0.3-0.4	12158
0.4-0.5	6202
0.5-0.6	3871
0.6-0.7	7185
0.7-0.8	5313
0.8-0.85	896
0.85-0.9	474
0.9-0.95	203
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC294884
0.9845	High Similarity	NPC158142
0.9845	High Similarity	NPC108198
0.9845	High Similarity	NPC200557
0.9845	High Similarity	NPC69029
0.9845	High Similarity	NPC10314
0.9771	High Similarity	NPC184613
0.9769	High Similarity	NPC143139
0.9769	High Similarity	NPC202846
0.9767	High Similarity	NPC125649
0.9767	High Similarity	NPC209199
0.9766	High Similarity	NPC161958
0.9766	High Similarity	NPC14224
0.9695	High Similarity	NPC56329
0.9695	High Similarity	NPC242715
0.9692	High Similarity	NPC241241
0.9621	High Similarity	NPC6300
0.9621	High Similarity	NPC132804
0.9621	High Similarity	NPC29868
0.9621	High Similarity	NPC230124
0.9621	High Similarity	NPC275061
0.9621	High Similarity	NPC212942
0.9621	High Similarity	NPC114171
0.9621	High Similarity	NPC220344
0.9621	High Similarity	NPC79622
0.9621	High Similarity	NPC243996
0.9618	High Similarity	NPC30632
0.9615	High Similarity	NPC160697
0.9609	High Similarity	NPC126836
0.9549	High Similarity	NPC12668
0.9549	High Similarity	NPC308768
0.9545	High Similarity	NPC200935
0.9545	High Similarity	NPC266453
0.9545	High Similarity	NPC22902
0.9545	High Similarity	NPC230919
0.9474	High Similarity	NPC243759
0.9474	High Similarity	NPC105847
0.9474	High Similarity	NPC218131
0.947	High Similarity	NPC205442
0.9407	High Similarity	NPC175838
0.9407	High Similarity	NPC183709
0.9407	High Similarity	NPC191231
0.9398	High Similarity	NPC151656
0.9398	High Similarity	NPC266006
0.9389	High Similarity	NPC32778
0.9385	High Similarity	NPC15543
0.9375	High Similarity	NPC127587
0.9375	High Similarity	NPC124452
0.9375	High Similarity	NPC82679
0.9375	High Similarity	NPC159968
0.9375	High Similarity	NPC236791
0.9375	High Similarity	NPC282000
0.9375	High Similarity	NPC324112
0.9375	High Similarity	NPC74817
0.9375	High Similarity	NPC169474
0.9375	High Similarity	NPC293054
0.9375	High Similarity	NPC246620
0.9333	High Similarity	NPC472089
0.9318	High Similarity	NPC7515
0.9318	High Similarity	NPC289258
0.9318	High Similarity	NPC311256
0.9318	High Similarity	NPC276026
0.9318	High Similarity	NPC206737
0.9318	High Similarity	NPC56764
0.9318	High Similarity	NPC469659
0.9318	High Similarity	NPC188378
0.9318	High Similarity	NPC555
0.9313	High Similarity	NPC6451
0.9302	High Similarity	NPC154866
0.9302	High Similarity	NPC28765
0.9297	High Similarity	NPC223136
0.9297	High Similarity	NPC28730
0.9297	High Similarity	NPC103823
0.9297	High Similarity	NPC44748
0.9297	High Similarity	NPC18924
0.9297	High Similarity	NPC76451
0.9297	High Similarity	NPC214406
0.9297	High Similarity	NPC78974
0.927	High Similarity	NPC469795
0.9265	High Similarity	NPC472088
0.9265	High Similarity	NPC472087
0.9259	High Similarity	NPC472090
0.9259	High Similarity	NPC73505
0.9259	High Similarity	NPC165026
0.9259	High Similarity	NPC34431
0.9259	High Similarity	NPC295719
0.9259	High Similarity	NPC472091
0.9259	High Similarity	NPC472092
0.9254	High Similarity	NPC73535
0.9254	High Similarity	NPC25111
0.9254	High Similarity	NPC201145
0.9254	High Similarity	NPC90615
0.9254	High Similarity	NPC272157
0.9254	High Similarity	NPC6262
0.9248	High Similarity	NPC240279
0.9248	High Similarity	NPC180602
0.9248	High Similarity	NPC214853
0.9248	High Similarity	NPC55239
0.9237	High Similarity	NPC474356
0.9237	High Similarity	NPC232275
0.9237	High Similarity	NPC45715
0.9237	High Similarity	NPC12275
0.9225	High Similarity	NPC252131
0.9225	High Similarity	NPC266555
0.9225	High Similarity	NPC236760
0.9225	High Similarity	NPC471986
0.9219	High Similarity	NPC299584
0.9219	High Similarity	NPC298757
0.9219	High Similarity	NPC57490
0.9219	High Similarity	NPC228771
0.9219	High Similarity	NPC251855
0.9219	High Similarity	NPC116907
0.9219	High Similarity	NPC221077
0.9219	High Similarity	NPC265483
0.9219	High Similarity	NPC472093
0.9219	High Similarity	NPC266705
0.9219	High Similarity	NPC117214
0.9219	High Similarity	NPC60885
0.9219	High Similarity	NPC82483
0.9219	High Similarity	NPC208950
0.9219	High Similarity	NPC29008
0.9219	High Similarity	NPC234400
0.9219	High Similarity	NPC233410
0.9219	High Similarity	NPC105925
0.9219	High Similarity	NPC203133
0.9219	High Similarity	NPC193544
0.9219	High Similarity	NPC475169
0.9219	High Similarity	NPC17943
0.9197	High Similarity	NPC469630
0.9185	High Similarity	NPC70682
0.9185	High Similarity	NPC260741
0.9179	High Similarity	NPC300846
0.9179	High Similarity	NPC162659
0.9179	High Similarity	NPC476639
0.9179	High Similarity	NPC114155
0.9179	High Similarity	NPC270456
0.9179	High Similarity	NPC133025
0.9179	High Similarity	NPC248727
0.9179	High Similarity	NPC265433
0.9173	High Similarity	NPC317380
0.9167	High Similarity	NPC228843
0.916	High Similarity	NPC234488
0.916	High Similarity	NPC224157
0.916	High Similarity	NPC311680
0.916	High Similarity	NPC299221
0.916	High Similarity	NPC192687
0.916	High Similarity	NPC51840
0.9147	High Similarity	NPC170485
0.9147	High Similarity	NPC223953
0.9137	High Similarity	NPC112251
0.913	High Similarity	NPC473108
0.9124	High Similarity	NPC470917
0.9124	High Similarity	NPC277784
0.9111	High Similarity	NPC156948
0.9111	High Similarity	NPC46277
0.9111	High Similarity	NPC86605
0.9111	High Similarity	NPC3072
0.9111	High Similarity	NPC301765
0.9104	High Similarity	NPC261873
0.9104	High Similarity	NPC256262
0.9104	High Similarity	NPC111655
0.9104	High Similarity	NPC283009
0.9091	High Similarity	NPC149337
0.9091	High Similarity	NPC471983
0.9091	High Similarity	NPC474017
0.9084	High Similarity	NPC58164
0.9084	High Similarity	NPC10225
0.9084	High Similarity	NPC212015
0.9084	High Similarity	NPC190144
0.9071	High Similarity	NPC262297
0.907	High Similarity	NPC113495
0.907	High Similarity	NPC9067
0.9062	High Similarity	NPC228922
0.9062	High Similarity	NPC233526
0.9062	High Similarity	NPC197757
0.9062	High Similarity	NPC95168
0.9062	High Similarity	NPC282496
0.9062	High Similarity	NPC136319
0.9062	High Similarity	NPC121115
0.9051	High Similarity	NPC35216
0.9051	High Similarity	NPC71046
0.9051	High Similarity	NPC265075
0.9044	High Similarity	NPC471183
0.9044	High Similarity	NPC127218
0.9044	High Similarity	NPC245207
0.9044	High Similarity	NPC25966
0.9044	High Similarity	NPC32630
0.9044	High Similarity	NPC55947
0.9044	High Similarity	NPC319647
0.9037	High Similarity	NPC234952
0.903	High Similarity	NPC103967
0.903	High Similarity	NPC471942
0.9023	High Similarity	NPC86655
0.9023	High Similarity	NPC202762
0.9023	High Similarity	NPC127624
0.9008	High Similarity	NPC266691
0.9008	High Similarity	NPC206615
0.9008	High Similarity	NPC186843
0.9008	High Similarity	NPC307050
0.9008	High Similarity	NPC98631

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 NPC313081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	953
0.2-0.3	1666
0.3-0.4	2814
0.4-0.5	1647
0.5-0.6	894
0.6-0.7	627
0.7-0.8	149
0.8-0.85	12
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD3027	Phase 3
0.8722	High Similarity	NPD1529	Clinical (unspecified phase)
0.8647	High Similarity	NPD1530	Clinical (unspecified phase)
0.8603	High Similarity	NPD1612	Clinical (unspecified phase)
0.8603	High Similarity	NPD1613	Approved
0.8456	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD4908	Phase 1
0.8382	Intermediate Similarity	NPD4625	Phase 3
0.8333	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3620	Phase 2
0.8289	Intermediate Similarity	NPD6234	Discontinued
0.8235	Intermediate Similarity	NPD3018	Phase 2
0.8203	Intermediate Similarity	NPD5283	Phase 1
0.82	Intermediate Similarity	NPD37	Approved
0.8195	Intermediate Similarity	NPD1610	Phase 2
0.8074	Intermediate Similarity	NPD4749	Approved
0.8074	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD2983	Phase 2
0.8047	Intermediate Similarity	NPD228	Approved
0.8039	Intermediate Similarity	NPD4966	Approved
0.8039	Intermediate Similarity	NPD4965	Approved
0.8039	Intermediate Similarity	NPD4967	Phase 2
0.8029	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD2981	Phase 2
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7943	Intermediate Similarity	NPD4060	Phase 1
0.7929	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7228	Approved
0.7895	Intermediate Similarity	NPD1548	Phase 1
0.7891	Intermediate Similarity	NPD3022	Approved
0.7891	Intermediate Similarity	NPD3021	Approved
0.7877	Intermediate Similarity	NPD6674	Discontinued
0.7843	Intermediate Similarity	NPD1934	Approved
0.7834	Intermediate Similarity	NPD7199	Phase 2
0.781	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2801	Approved
0.7792	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2861	Phase 2
0.7708	Intermediate Similarity	NPD4097	Suspended
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD4005	Discontinued
0.7619	Intermediate Similarity	NPD3540	Phase 1
0.7615	Intermediate Similarity	NPD4750	Phase 3
0.758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3882	Suspended
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD6099	Approved
0.7551	Intermediate Similarity	NPD3539	Phase 1
0.755	Intermediate Similarity	NPD1511	Approved
0.7536	Intermediate Similarity	NPD3705	Approved
0.7518	Intermediate Similarity	NPD4624	Approved
0.7518	Intermediate Similarity	NPD4626	Approved
0.7517	Intermediate Similarity	NPD3657	Discovery
0.7517	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8054	Approved
0.7485	Intermediate Similarity	NPD8053	Approved
0.7483	Intermediate Similarity	NPD7124	Phase 2
0.7468	Intermediate Similarity	NPD1653	Approved
0.7452	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD1512	Approved
0.7448	Intermediate Similarity	NPD1558	Phase 1
0.7447	Intermediate Similarity	NPD3094	Phase 2
0.7431	Intermediate Similarity	NPD5109	Approved
0.7431	Intermediate Similarity	NPD5110	Phase 2
0.7431	Intermediate Similarity	NPD5111	Phase 2
0.7421	Intermediate Similarity	NPD4055	Discovery
0.7417	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7240	Approved
0.741	Intermediate Similarity	NPD3092	Approved
0.7386	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5762	Approved
0.7383	Intermediate Similarity	NPD5763	Approved
0.7376	Intermediate Similarity	NPD8651	Approved
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD3892	Phase 2
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7338	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4357	Discontinued
0.732	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7041	Phase 2
0.732	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5327	Phase 3
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.7297	Intermediate Similarity	NPD6111	Discontinued
0.7296	Intermediate Similarity	NPD3817	Phase 2
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7074	Phase 3
0.7286	Intermediate Similarity	NPD422	Phase 1
0.7285	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD7447	Phase 1
0.7273	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1242	Phase 1
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.7256	Intermediate Similarity	NPD27	Approved
0.7256	Intermediate Similarity	NPD2489	Approved
0.7254	Intermediate Similarity	NPD1283	Approved
0.7254	Intermediate Similarity	NPD6696	Suspended
0.7248	Intermediate Similarity	NPD1510	Phase 2
0.7246	Intermediate Similarity	NPD3091	Approved
0.7241	Intermediate Similarity	NPD7095	Approved
0.7239	Intermediate Similarity	NPD3051	Approved
0.7235	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7819	Suspended
0.723	Intermediate Similarity	NPD1607	Approved
0.7229	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD5494	Approved
0.7219	Intermediate Similarity	NPD4577	Approved
0.7219	Intermediate Similarity	NPD4578	Approved
0.7215	Intermediate Similarity	NPD5090	Approved
0.7215	Intermediate Similarity	NPD5089	Approved
0.7211	Intermediate Similarity	NPD4140	Approved
0.7211	Intermediate Similarity	NPD2238	Phase 2
0.7211	Intermediate Similarity	NPD1240	Approved
0.7208	Intermediate Similarity	NPD7213	Phase 3
0.7208	Intermediate Similarity	NPD7212	Phase 2
0.7197	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2342	Discontinued
0.7195	Intermediate Similarity	NPD2970	Approved
0.7195	Intermediate Similarity	NPD2969	Approved
0.7194	Intermediate Similarity	NPD5691	Approved
0.7194	Intermediate Similarity	NPD1651	Approved
0.7193	Intermediate Similarity	NPD4663	Approved
0.719	Intermediate Similarity	NPD5241	Discontinued
0.719	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3020	Approved
0.7188	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7472	Approved
0.7185	Intermediate Similarity	NPD7635	Approved
0.7178	Intermediate Similarity	NPD6959	Discontinued
0.7171	Intermediate Similarity	NPD3060	Approved
0.7162	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD7549	Discontinued
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7153	Intermediate Similarity	NPD7157	Approved
0.7153	Intermediate Similarity	NPD6671	Approved
0.7152	Intermediate Similarity	NPD4678	Approved
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD4675	Approved
0.7151	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD2684	Approved
0.7134	Intermediate Similarity	NPD7229	Phase 3
0.7133	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6331	Phase 2
0.7124	Intermediate Similarity	NPD8166	Discontinued
0.7118	Intermediate Similarity	NPD7311	Approved
0.7118	Intermediate Similarity	NPD7310	Approved
0.7118	Intermediate Similarity	NPD7313	Approved
0.7118	Intermediate Similarity	NPD7312	Approved
0.7114	Intermediate Similarity	NPD6353	Approved
0.7114	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2232	Approved
0.7113	Intermediate Similarity	NPD2233	Approved
0.7113	Intermediate Similarity	NPD2230	Approved
0.7105	Intermediate Similarity	NPD7037	Approved
0.7099	Intermediate Similarity	NPD7833	Phase 2
0.7099	Intermediate Similarity	NPD7831	Phase 2
0.7099	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7095	Intermediate Similarity	NPD943	Approved
0.709	Intermediate Similarity	NPD5451	Approved
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7079	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2677	Approved
0.7078	Intermediate Similarity	NPD2219	Phase 1
0.7076	Intermediate Similarity	NPD7309	Approved
0.7075	Intermediate Similarity	NPD3144	Approved
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7075	Intermediate Similarity	NPD3145	Approved
0.7071	Intermediate Similarity	NPD1357	Approved
0.7067	Intermediate Similarity	NPD4538	Approved
0.7067	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4536	Approved
0.7066	Intermediate Similarity	NPD8251	Approved
0.7066	Intermediate Similarity	NPD8099	Discontinued
0.7066	Intermediate Similarity	NPD8252	Approved
0.7063	Intermediate Similarity	NPD1669	Approved
0.7059	Intermediate Similarity	NPD7843	Approved
0.7051	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2532	Approved
0.7051	Intermediate Similarity	NPD2534	Approved
0.7051	Intermediate Similarity	NPD2533	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data