NPASS Compound

Structure

CID80918 OpenBabel06191715422D 35 40 0 0 1 0 0 0 0 0999 V2000 -2.4863 4.7147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0315 4.0266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1262 5.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6384 4.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5125 -1.8639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0247 -0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6630 3.0324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 2.9304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9222 4.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6914 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7681 4.8832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 -1.4650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0763 2.9301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7677 1.9533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0760 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0603 3.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9221 3.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6915 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 1.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0762 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2298 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7678 2.9299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9219 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5378 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2299 1.4652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5379 1.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8458 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6138 4.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -0.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0201 1.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9218 0.4879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3842 1.9536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6137 3.4181 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 14 23 1 0 0 0 0 15 32 1 0 0 0 0 17 22 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 19 27 2 0 0 0 0 20 23 2 0 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 34 1 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 25 31 1 0 0 0 0 26 20 1 6 0 0 0 26 33 1 0 0 0 0 27 33 1 0 0 0 0 28 35 1 0 0 0 0 29 34 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.22
Volume:	496.32
LogP:	8.308
LogD:	5.679
LogS:	-2.287
# Rotatable Bonds:	2
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	4.555
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.941
MDCK Permeability:	1.4414549696084578e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.325
20% Bioavailability (F20%):	0.437
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	97.91211700439453%
Volume Distribution (VD):	2.239
Pgp-substrate:	7.31512975692749%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.65
CYP2C19-inhibitor:	0.773
CYP2C19-substrate:	0.708
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.744

ADMET: Excretion

Clearance (CL):	1.849
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.749
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.428
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.682
Carcinogencity:	0.736
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.775

Download Data

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

Natural Product: NPC80918

Natural Product ID:	NPC80918
*Common Name:**	Lespecyrtin E4
IUPAC Name:	n.a.
Synonyms:	Lespecyrtin E4
Standard InCHIKey:	MYOQMGSQVOTIII-LVXARBLLSA-N
Standard InCHI:	InChI=1S/C30H32O5/c1-16(2)7-8-19-25(31)28-18(10-12-30(5,6)35-28)24-21-15-32-23-14-22-17(9-11-29(3,4)34-22)13-20(23)26(21)33-27(19)24/h7,9-14,21,26,31H,8,15H2,1-6H3/t21-,26-/m0/s1
SMILES:	CC(=CCc1c2O[C@@H]3[C@H](c2c2c(c1O)OC(C=C2)(C)C)COc1c3cc2C=CC(Oc2c1)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557492
PubChem CID:	25208756
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10080	Teucrium betonicum	Species	Lamiaceae	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
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	=	4500.0	nM	PMID[538606]

☑ 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 NPC80918 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	492
0.1-0.2	1605
0.2-0.3	4121
0.3-0.4	10778
0.4-0.5	7802
0.5-0.6	3893
0.6-0.7	7308
0.7-0.8	5256
0.8-0.85	924
0.85-0.9	426
0.9-0.95	87
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188578
0.9863	High Similarity	NPC160196
0.9521	High Similarity	NPC21776
0.9521	High Similarity	NPC16269
0.9452	High Similarity	NPC233980
0.9384	High Similarity	NPC469557
0.9315	High Similarity	NPC63879
0.9315	High Similarity	NPC45257
0.9315	High Similarity	NPC93323
0.9315	High Similarity	NPC12641
0.9315	High Similarity	NPC280092
0.9315	High Similarity	NPC50250
0.9267	High Similarity	NPC2745
0.9257	High Similarity	NPC101376
0.9257	High Similarity	NPC474397
0.9247	High Similarity	NPC47633
0.9247	High Similarity	NPC85264
0.9247	High Similarity	NPC102044
0.9205	High Similarity	NPC157783
0.9205	High Similarity	NPC325860
0.92	High Similarity	NPC195561
0.92	High Similarity	NPC158784
0.9184	High Similarity	NPC473108
0.9178	High Similarity	NPC107161
0.9178	High Similarity	NPC59841
0.9178	High Similarity	NPC2613
0.9178	High Similarity	NPC475891
0.9178	High Similarity	NPC204347
0.9139	High Similarity	NPC302915
0.9122	High Similarity	NPC221318
0.9116	High Similarity	NPC477616
0.9116	High Similarity	NPC258083
0.911	High Similarity	NPC265075
0.911	High Similarity	NPC247291
0.9085	High Similarity	NPC159922
0.9067	High Similarity	NPC473876
0.9067	High Similarity	NPC212142
0.9054	High Similarity	NPC469795
0.9054	High Similarity	NPC473845
0.9041	High Similarity	NPC27495
0.9041	High Similarity	NPC309124
0.9041	High Similarity	NPC259519
0.9041	High Similarity	NPC184797
0.9041	High Similarity	NPC160283
0.9041	High Similarity	NPC254759
0.8993	High Similarity	NPC90645
0.8986	High Similarity	NPC474104
0.898	High Similarity	NPC471389
0.898	High Similarity	NPC263261
0.898	High Similarity	NPC87725
0.8973	High Similarity	NPC70682
0.8973	High Similarity	NPC25966
0.8973	High Similarity	NPC292882
0.8973	High Similarity	NPC236306
0.8973	High Similarity	NPC245207
0.8973	High Similarity	NPC232164
0.8973	High Similarity	NPC260741
0.8973	High Similarity	NPC473739
0.8973	High Similarity	NPC32630
0.8973	High Similarity	NPC127218
0.8973	High Similarity	NPC319647
0.8933	High Similarity	NPC260397
0.8904	High Similarity	NPC276490
0.8904	High Similarity	NPC474282
0.8904	High Similarity	NPC107551
0.8904	High Similarity	NPC326797
0.8904	High Similarity	NPC103976
0.8904	High Similarity	NPC102904
0.8904	High Similarity	NPC176051
0.8882	High Similarity	NPC476969
0.8867	High Similarity	NPC472457
0.8851	High Similarity	NPC35216
0.8851	High Similarity	NPC71046
0.8851	High Similarity	NPC311530
0.8844	High Similarity	NPC471388
0.8839	High Similarity	NPC157333
0.8836	High Similarity	NPC474639
0.8836	High Similarity	NPC162659
0.8836	High Similarity	NPC270456
0.8836	High Similarity	NPC248727
0.8836	High Similarity	NPC227503
0.8836	High Similarity	NPC173660
0.8836	High Similarity	NPC234952
0.8836	High Similarity	NPC265433
0.8836	High Similarity	NPC20829
0.8836	High Similarity	NPC126101
0.8836	High Similarity	NPC230734
0.8836	High Similarity	NPC18189
0.8836	High Similarity	NPC262585
0.8824	High Similarity	NPC477612
0.8816	High Similarity	NPC20757
0.8816	High Similarity	NPC227516
0.8808	High Similarity	NPC211758
0.8808	High Similarity	NPC112251
0.8808	High Similarity	NPC87794
0.8792	High Similarity	NPC175838
0.8792	High Similarity	NPC323126
0.8784	High Similarity	NPC234568
0.8784	High Similarity	NPC198038
0.8776	High Similarity	NPC477938
0.8776	High Similarity	NPC35550
0.8776	High Similarity	NPC211549
0.8767	High Similarity	NPC112939
0.8767	High Similarity	NPC151224
0.8767	High Similarity	NPC94750
0.8767	High Similarity	NPC474206
0.8767	High Similarity	NPC121812
0.8767	High Similarity	NPC473413
0.8767	High Similarity	NPC134968
0.8767	High Similarity	NPC470356
0.8767	High Similarity	NPC195022
0.8767	High Similarity	NPC112246
0.8758	High Similarity	NPC211561
0.8742	High Similarity	NPC307466
0.8742	High Similarity	NPC181615
0.8733	High Similarity	NPC173203
0.8733	High Similarity	NPC163508
0.8733	High Similarity	NPC81638
0.8716	High Similarity	NPC212942
0.8716	High Similarity	NPC184613
0.8716	High Similarity	NPC19869
0.8716	High Similarity	NPC29868
0.8716	High Similarity	NPC475836
0.8716	High Similarity	NPC79622
0.871	High Similarity	NPC476391
0.8707	High Similarity	NPC327735
0.8707	High Similarity	NPC29799
0.8707	High Similarity	NPC156502
0.8707	High Similarity	NPC472334
0.8707	High Similarity	NPC306441
0.8707	High Similarity	NPC470802
0.8707	High Similarity	NPC302701
0.8707	High Similarity	NPC263367
0.8707	High Similarity	NPC10737
0.8707	High Similarity	NPC472800
0.8707	High Similarity	NPC477939
0.8707	High Similarity	NPC472336
0.8707	High Similarity	NPC54743
0.8707	High Similarity	NPC177160
0.8707	High Similarity	NPC16435
0.8707	High Similarity	NPC269091
0.8707	High Similarity	NPC209985
0.8701	High Similarity	NPC472710
0.8701	High Similarity	NPC472709
0.8699	High Similarity	NPC124085
0.8699	High Similarity	NPC97834
0.8699	High Similarity	NPC296915
0.8699	High Similarity	NPC115335
0.8699	High Similarity	NPC225696
0.8699	High Similarity	NPC106215
0.8699	High Similarity	NPC317380
0.8699	High Similarity	NPC187616
0.8699	High Similarity	NPC117048
0.8699	High Similarity	NPC193026
0.8699	High Similarity	NPC474478
0.8699	High Similarity	NPC49603
0.8699	High Similarity	NPC223008
0.8699	High Similarity	NPC198154
0.8693	High Similarity	NPC329836
0.8693	High Similarity	NPC261502
0.8693	High Similarity	NPC71726
0.8693	High Similarity	NPC166584
0.8693	High Similarity	NPC301961
0.8693	High Similarity	NPC281549
0.8684	High Similarity	NPC324492
0.8684	High Similarity	NPC317053
0.8675	High Similarity	NPC44530
0.8675	High Similarity	NPC277951
0.8675	High Similarity	NPC304894
0.8675	High Similarity	NPC317237
0.8675	High Similarity	NPC15659
0.8667	High Similarity	NPC186033
0.8662	High Similarity	NPC202104
0.8658	High Similarity	NPC12668
0.8658	High Similarity	NPC34431
0.8658	High Similarity	NPC165026
0.8658	High Similarity	NPC308768
0.8658	High Similarity	NPC73505
0.8658	High Similarity	NPC295719
0.8649	High Similarity	NPC474687
0.8649	High Similarity	NPC56329
0.8649	High Similarity	NPC242715
0.8639	High Similarity	NPC164787
0.8639	High Similarity	NPC260898
0.8639	High Similarity	NPC61946
0.8639	High Similarity	NPC472337
0.8639	High Similarity	NPC47398
0.8639	High Similarity	NPC234333
0.8639	High Similarity	NPC313081
0.8636	High Similarity	NPC321657
0.8636	High Similarity	NPC318373
0.8636	High Similarity	NPC10010
0.863	High Similarity	NPC92805
0.863	High Similarity	NPC11060
0.863	High Similarity	NPC36661
0.863	High Similarity	NPC168059
0.863	High Similarity	NPC105554
0.863	High Similarity	NPC158331
0.863	High Similarity	NPC85435
0.863	High Similarity	NPC77196

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 NPC80918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	904
0.2-0.3	1908
0.3-0.4	2791
0.4-0.5	1556
0.5-0.6	896
0.6-0.7	555
0.7-0.8	124
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1613	Approved
0.8288	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3027	Phase 3
0.8231	Intermediate Similarity	NPD4625	Phase 3
0.8219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD6674	Discontinued
0.8041	Intermediate Similarity	NPD4908	Phase 1
0.8036	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7973	Intermediate Similarity	NPD2861	Phase 2
0.7939	Intermediate Similarity	NPD6234	Discontinued
0.7933	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD4749	Approved
0.7808	Intermediate Similarity	NPD1610	Phase 2
0.7805	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5494	Approved
0.777	Intermediate Similarity	NPD6696	Suspended
0.7744	Intermediate Similarity	NPD37	Approved
0.7744	Intermediate Similarity	NPD1934	Approved
0.7716	Intermediate Similarity	NPD1653	Approved
0.7711	Intermediate Similarity	NPD4965	Approved
0.7711	Intermediate Similarity	NPD4966	Approved
0.7711	Intermediate Similarity	NPD4967	Phase 2
0.7697	Intermediate Similarity	NPD2801	Approved
0.7657	Intermediate Similarity	NPD7313	Approved
0.7657	Intermediate Similarity	NPD7311	Approved
0.7657	Intermediate Similarity	NPD7310	Approved
0.7657	Intermediate Similarity	NPD7312	Approved
0.7614	Intermediate Similarity	NPD7309	Approved
0.7602	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6166	Phase 2
0.7597	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4060	Phase 1
0.7597	Intermediate Similarity	NPD3620	Phase 2
0.7584	Intermediate Similarity	NPD7906	Approved
0.7572	Intermediate Similarity	NPD7054	Approved
0.7548	Intermediate Similarity	NPD5124	Phase 1
0.7548	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7240	Approved
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7529	Intermediate Similarity	NPD7472	Approved
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7528	Intermediate Similarity	NPD4663	Approved
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7549	Discontinued
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD6100	Approved
0.7458	Intermediate Similarity	NPD4578	Approved
0.7458	Intermediate Similarity	NPD4577	Approved
0.7457	Intermediate Similarity	NPD7473	Discontinued
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6959	Discontinued
0.7414	Intermediate Similarity	NPD3818	Discontinued
0.7399	Intermediate Similarity	NPD2489	Approved
0.7399	Intermediate Similarity	NPD27	Approved
0.7397	Intermediate Similarity	NPD7340	Approved
0.7396	Intermediate Similarity	NPD3882	Suspended
0.7384	Intermediate Similarity	NPD6232	Discontinued
0.7381	Intermediate Similarity	NPD5929	Approved
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.7341	Intermediate Similarity	NPD2970	Approved
0.7341	Intermediate Similarity	NPD2969	Approved
0.7329	Intermediate Similarity	NPD6671	Approved
0.7325	Intermediate Similarity	NPD5735	Approved
0.7318	Intermediate Similarity	NPD8054	Approved
0.7318	Intermediate Similarity	NPD8053	Approved
0.7317	Intermediate Similarity	NPD7447	Phase 1
0.7312	Intermediate Similarity	NPD5762	Approved
0.7312	Intermediate Similarity	NPD5763	Approved
0.7305	Intermediate Similarity	NPD4380	Phase 2
0.7303	Intermediate Similarity	NPD7808	Phase 3
0.7303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6797	Phase 2
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3051	Approved
0.7278	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7256	Intermediate Similarity	NPD1511	Approved
0.7256	Intermediate Similarity	NPD7213	Phase 3
0.7256	Intermediate Similarity	NPD7212	Phase 2
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6559	Discontinued
0.7237	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3705	Approved
0.7212	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5058	Phase 3
0.7192	Intermediate Similarity	NPD1398	Phase 1
0.7192	Intermediate Similarity	NPD5283	Phase 1
0.719	Intermediate Similarity	NPD8651	Approved
0.7188	Intermediate Similarity	NPD5588	Approved
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD6331	Phase 2
0.7178	Intermediate Similarity	NPD7466	Approved
0.7176	Intermediate Similarity	NPD7819	Suspended
0.7175	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1512	Approved
0.7169	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD7075	Discontinued
0.7135	Intermediate Similarity	NPD3817	Phase 2
0.7127	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4538	Approved
0.7125	Intermediate Similarity	NPD4536	Approved
0.7125	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD5327	Phase 3
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7108	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7266	Discontinued
0.7095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5125	Phase 3
0.7086	Intermediate Similarity	NPD5126	Approved
0.7081	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3892	Phase 2
0.7073	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD6353	Approved
0.7063	Intermediate Similarity	NPD4097	Suspended
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD228	Approved
0.7052	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7041	Phase 2
0.7041	Intermediate Similarity	NPD4005	Discontinued
0.7041	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5402	Approved
0.7029	Intermediate Similarity	NPD8127	Discontinued
0.7025	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7985	Registered
0.7022	Intermediate Similarity	NPD3751	Discontinued
0.7019	Intermediate Similarity	NPD7097	Phase 1
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7007	Intermediate Similarity	NPD7635	Approved
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD1611	Approved
0.6993	Remote Similarity	NPD1091	Approved
0.6989	Remote Similarity	NPD6071	Discontinued
0.6983	Remote Similarity	NPD8156	Discontinued
0.6978	Remote Similarity	NPD8313	Approved
0.6978	Remote Similarity	NPD8312	Approved
0.6977	Remote Similarity	NPD8455	Phase 2
0.6975	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5960	Phase 3
0.6975	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6090	Discontinued
0.6963	Remote Similarity	NPD2494	Approved
0.6963	Remote Similarity	NPD2493	Approved
0.6954	Remote Similarity	NPD7831	Phase 2
0.6954	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7833	Phase 2
0.6951	Remote Similarity	NPD2424	Discontinued
0.6951	Remote Similarity	NPD7037	Approved
0.6943	Remote Similarity	NPD4582	Approved
0.6943	Remote Similarity	NPD4583	Approved
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4140	Approved
0.6937	Remote Similarity	NPD1558	Phase 1
0.6936	Remote Similarity	NPD2560	Approved
0.6936	Remote Similarity	NPD2563	Approved
0.6932	Remote Similarity	NPD1247	Approved
0.6928	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2677	Approved
0.6927	Remote Similarity	NPD8099	Discontinued
0.6927	Remote Similarity	NPD8252	Approved
0.6927	Remote Similarity	NPD8251	Approved
0.6923	Remote Similarity	NPD3094	Phase 2
0.6918	Remote Similarity	NPD3022	Approved
0.6918	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3021	Approved
0.691	Remote Similarity	NPD4481	Phase 3
0.6909	Remote Similarity	NPD5177	Phase 3
0.6905	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4678	Approved
0.6901	Remote Similarity	NPD4675	Approved
0.6897	Remote Similarity	NPD7768	Phase 2
0.6894	Remote Similarity	NPD3657	Discovery
0.6891	Remote Similarity	NPD4004	Approved
0.6891	Remote Similarity	NPD4002	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