NPASS Compound

Structure

CID27187 OpenBabel06191715352D 30 33 0 0 1 0 0 0 0 0999 V2000 2.5160 4.4963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 4.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 3.3262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2742 2.8084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3859 -1.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6364 2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0288 1.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5155 2.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6763 0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 -1.9356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6771 0.9673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3528 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6765 -1.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6367 3.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3277 2.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5146 -1.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5152 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8382 -1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6769 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -1.4522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3530 0.9668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5147 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5144 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8380 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8383 -0.4840 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2323 1.4742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3804 0.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5145 -1.4525 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 22 2 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 23 2 0 0 0 0 21 13 1 1 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 20 1 1 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.21
Volume:	438.095
LogP:	7.351
LogD:	4.402
LogS:	-3.282
# Rotatable Bonds:	4
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	3.989
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	1.552937646920327e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	93.04364776611328%
Volume Distribution (VD):	4.068
Pgp-substrate:	9.975830078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.8
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.305
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.487
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.407

ADMET: Excretion

Clearance (CL):	14.607
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.13
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.417
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.942
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.692
Respiratory Toxicity:	0.702

Download Data

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

Natural Product: NPC27187

Natural Product ID:	NPC27187
*Common Name:**	Lespeflorin G4
IUPAC Name:	(6aR,11aR)-8-methyl-2,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:	Lespeflorin G4
Standard InCHIKey:	RBWZJDQLHCNCDG-LVXARBLLSA-N
Standard InCHI:	InChI=1S/C26H30O4/c1-14(2)6-8-17-11-20-23(12-22(17)27)29-13-21-19-10-16(5)24(28)18(9-7-15(3)4)25(19)30-26(20)21/h6-7,10-12,21,26-28H,8-9,13H2,1-5H3/t21-,26-/m0/s1
SMILES:	CC(=CCc1cc2c(cc1O)OC[C@H]1c3cc(C)c(c(CC=C(C)C)c3O[C@@H]21)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562032
PubChem CID:	25243081
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]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
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]
NPO13293	Lespedeza floribunda	Species	Fabaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3240.0	nM	PMID[456429]
NPT2	Others	Unspecified		IC50	=	3200.0	nM	PMID[456430]

☑ 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 NPC27187 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	372
0.1-0.2	1443
0.2-0.3	3777
0.3-0.4	11461
0.4-0.5	7452
0.5-0.6	4129
0.6-0.7	7743
0.7-0.8	5100
0.8-0.85	897
0.85-0.9	200
0.9-0.95	66
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470225
0.9919	High Similarity	NPC271945
0.9919	High Similarity	NPC206224
0.9919	High Similarity	NPC118114
0.9919	High Similarity	NPC12875
0.9919	High Similarity	NPC207892
0.9919	High Similarity	NPC228369
0.9919	High Similarity	NPC268917
0.9919	High Similarity	NPC129784
0.9919	High Similarity	NPC17343
0.9919	High Similarity	NPC476166
0.9919	High Similarity	NPC129106
0.9919	High Similarity	NPC164574
0.9919	High Similarity	NPC280653
0.9919	High Similarity	NPC236014
0.9919	High Similarity	NPC196765
0.9919	High Similarity	NPC181497
0.9919	High Similarity	NPC300875
0.9919	High Similarity	NPC150011
0.984	High Similarity	NPC13005
0.9685	High Similarity	NPC296915
0.9685	High Similarity	NPC223008
0.9685	High Similarity	NPC115335
0.9685	High Similarity	NPC198154
0.9685	High Similarity	NPC225696
0.9685	High Similarity	NPC97834
0.9677	High Similarity	NPC38664
0.9677	High Similarity	NPC53986
0.9677	High Similarity	NPC39064
0.9677	High Similarity	NPC47283
0.9606	High Similarity	NPC85435
0.96	High Similarity	NPC93962
0.9531	High Similarity	NPC117048
0.9531	High Similarity	NPC124085
0.952	High Similarity	NPC274717
0.9516	High Similarity	NPC471215
0.9516	High Similarity	NPC26879
0.9516	High Similarity	NPC262573
0.9516	High Similarity	NPC283049
0.9516	High Similarity	NPC50315
0.9516	High Similarity	NPC230479
0.9462	High Similarity	NPC474687
0.9449	High Similarity	NPC244888
0.9449	High Similarity	NPC118683
0.9449	High Similarity	NPC68205
0.9449	High Similarity	NPC162801
0.9449	High Similarity	NPC293203
0.9449	High Similarity	NPC164804
0.9449	High Similarity	NPC211413
0.9435	High Similarity	NPC188022
0.9435	High Similarity	NPC103420
0.9435	High Similarity	NPC285040
0.9435	High Similarity	NPC17809
0.9435	High Similarity	NPC102540
0.9389	High Similarity	NPC475836
0.9385	High Similarity	NPC18189
0.9385	High Similarity	NPC3049
0.9385	High Similarity	NPC262585
0.9385	High Similarity	NPC20829
0.936	High Similarity	NPC276212
0.9355	High Similarity	NPC294156
0.9355	High Similarity	NPC256015
0.9355	High Similarity	NPC106914
0.9355	High Similarity	NPC86502
0.9355	High Similarity	NPC197351
0.9355	High Similarity	NPC134195
0.9355	High Similarity	NPC246648
0.9302	High Similarity	NPC77196
0.9297	High Similarity	NPC103799
0.928	High Similarity	NPC81641
0.9274	High Similarity	NPC76465
0.9274	High Similarity	NPC38761
0.9248	High Similarity	NPC5155
0.9231	High Similarity	NPC473107
0.9194	High Similarity	NPC150026
0.9194	High Similarity	NPC36016
0.9194	High Similarity	NPC100099
0.916	High Similarity	NPC125579
0.9154	High Similarity	NPC92805
0.9141	High Similarity	NPC134360
0.9134	High Similarity	NPC149796
0.9113	High Similarity	NPC193364
0.9113	High Similarity	NPC54972
0.9111	High Similarity	NPC47633
0.9111	High Similarity	NPC85264
0.9111	High Similarity	NPC102044
0.9091	High Similarity	NPC471522
0.9062	High Similarity	NPC222572
0.9062	High Similarity	NPC87224
0.9044	High Similarity	NPC280092
0.9044	High Similarity	NPC45257
0.9044	High Similarity	NPC63879
0.9044	High Similarity	NPC93323
0.9044	High Similarity	NPC12641
0.903	High Similarity	NPC27495
0.903	High Similarity	NPC184797
0.903	High Similarity	NPC309124
0.9023	High Similarity	NPC470307
0.9023	High Similarity	NPC470308
0.9023	High Similarity	NPC477938
0.9015	High Similarity	NPC473413
0.9008	High Similarity	NPC215037
0.8978	High Similarity	NPC469557
0.8963	High Similarity	NPC247291
0.8963	High Similarity	NPC87725
0.8963	High Similarity	NPC263261
0.8955	High Similarity	NPC70682
0.8955	High Similarity	NPC236306
0.8955	High Similarity	NPC260741
0.8955	High Similarity	NPC232164
0.8955	High Similarity	NPC473739
0.8955	High Similarity	NPC32630
0.8952	High Similarity	NPC258979
0.8952	High Similarity	NPC93398
0.8952	High Similarity	NPC8283
0.8947	High Similarity	NPC470802
0.8947	High Similarity	NPC141717
0.8939	High Similarity	NPC476616
0.8939	High Similarity	NPC476617
0.8939	High Similarity	NPC476615
0.8931	High Similarity	NPC472798
0.8897	High Similarity	NPC107161
0.8889	High Similarity	NPC259519
0.8872	High Similarity	NPC15109
0.8872	High Similarity	NPC11727
0.8871	High Similarity	NPC172253
0.8871	High Similarity	NPC59561
0.8864	High Similarity	NPC11060
0.8864	High Similarity	NPC177712
0.8864	High Similarity	NPC24913
0.8855	High Similarity	NPC160623
0.8849	High Similarity	NPC101376
0.8849	High Similarity	NPC16269
0.8849	High Similarity	NPC21776
0.8846	High Similarity	NPC472795
0.8846	High Similarity	NPC472796
0.8846	High Similarity	NPC472797
0.8837	High Similarity	NPC473134
0.8828	High Similarity	NPC207179
0.8828	High Similarity	NPC278552
0.8828	High Similarity	NPC167571
0.8824	High Similarity	NPC277331
0.8824	High Similarity	NPC265075
0.8824	High Similarity	NPC100482
0.8824	High Similarity	NPC35216
0.8815	High Similarity	NPC471388
0.881	High Similarity	NPC476633
0.8806	High Similarity	NPC126101
0.8806	High Similarity	NPC78047
0.8806	High Similarity	NPC270456
0.8806	High Similarity	NPC472800
0.8806	High Similarity	NPC248727
0.8806	High Similarity	NPC234952
0.8806	High Similarity	NPC162659
0.8806	High Similarity	NPC173660
0.8806	High Similarity	NPC265433
0.8806	High Similarity	NPC327735
0.879	High Similarity	NPC131118
0.8786	High Similarity	NPC71726
0.8777	High Similarity	NPC260397
0.8769	High Similarity	NPC38604
0.8769	High Similarity	NPC211179
0.8768	High Similarity	NPC473108
0.8768	High Similarity	NPC475492
0.8759	High Similarity	NPC2613
0.8759	High Similarity	NPC204347
0.8759	High Similarity	NPC59841
0.8759	High Similarity	NPC475891
0.875	High Similarity	NPC213607
0.875	High Similarity	NPC182509
0.875	High Similarity	NPC174787
0.875	High Similarity	NPC254759
0.875	High Similarity	NPC160283
0.875	High Similarity	NPC159132
0.874	High Similarity	NPC57199
0.8731	High Similarity	NPC61946
0.8731	High Similarity	NPC470356
0.8731	High Similarity	NPC112246
0.8731	High Similarity	NPC260898
0.8731	High Similarity	NPC112939
0.8731	High Similarity	NPC195022
0.8731	High Similarity	NPC151224
0.8731	High Similarity	NPC474206
0.8731	High Similarity	NPC47398
0.8731	High Similarity	NPC234333
0.8731	High Similarity	NPC121812
0.8731	High Similarity	NPC94750
0.8722	High Similarity	NPC26394
0.872	High Similarity	NPC295259
0.8712	High Similarity	NPC472590
0.8705	High Similarity	NPC106126
0.8705	High Similarity	NPC181615
0.8705	High Similarity	NPC108994
0.8705	High Similarity	NPC180953
0.8686	High Similarity	NPC311530
0.8686	High Similarity	NPC108674
0.8686	High Similarity	NPC471389
0.8682	High Similarity	NPC293801
0.8676	High Similarity	NPC292882
0.8676	High Similarity	NPC127218

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 NPC27187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	890
0.2-0.3	1641
0.3-0.4	2702
0.4-0.5	1777
0.5-0.6	1059
0.6-0.7	629
0.7-0.8	138
0.8-0.85	7
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.937	High Similarity	NPD4907	Clinical (unspecified phase)
0.9213	High Similarity	NPD4908	Phase 1
0.9113	High Similarity	NPD1610	Phase 2
0.8692	High Similarity	NPD2861	Phase 2
0.864	High Similarity	NPD1548	Phase 1
0.8561	High Similarity	NPD4625	Phase 3
0.8527	High Similarity	NPD4749	Approved
0.8507	High Similarity	NPD1612	Clinical (unspecified phase)
0.8507	High Similarity	NPD1613	Approved
0.8496	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD5124	Phase 1
0.8175	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3027	Phase 3
0.8028	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7213	Phase 3
0.7931	Intermediate Similarity	NPD7212	Phase 2
0.7926	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7447	Phase 1
0.7872	Intermediate Similarity	NPD5588	Approved
0.7847	Intermediate Similarity	NPD7466	Approved
0.7842	Intermediate Similarity	NPD4060	Phase 1
0.7836	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1549	Phase 2
0.782	Intermediate Similarity	NPD422	Phase 1
0.7817	Intermediate Similarity	NPD6100	Approved
0.7817	Intermediate Similarity	NPD6099	Approved
0.7801	Intermediate Similarity	NPD4536	Approved
0.7801	Intermediate Similarity	NPD4538	Approved
0.7801	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6696	Suspended
0.7778	Intermediate Similarity	NPD8651	Approved
0.774	Intermediate Similarity	NPD5058	Phase 3
0.7733	Intermediate Similarity	NPD4380	Phase 2
0.7724	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6671	Approved
0.7687	Intermediate Similarity	NPD1091	Approved
0.7662	Intermediate Similarity	NPD7075	Discontinued
0.7639	Intermediate Similarity	NPD6005	Phase 3
0.7639	Intermediate Similarity	NPD6004	Phase 3
0.7639	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6002	Phase 3
0.7632	Intermediate Similarity	NPD37	Approved
0.7632	Intermediate Similarity	NPD1934	Approved
0.7628	Intermediate Similarity	NPD6959	Discontinued
0.7622	Intermediate Similarity	NPD5960	Phase 3
0.7613	Intermediate Similarity	NPD6234	Discontinued
0.7603	Intermediate Similarity	NPD3750	Approved
0.7603	Intermediate Similarity	NPD3892	Phase 2
0.7597	Intermediate Similarity	NPD7768	Phase 2
0.7597	Intermediate Similarity	NPD4966	Approved
0.7597	Intermediate Similarity	NPD4965	Approved
0.7597	Intermediate Similarity	NPD4967	Phase 2
0.7582	Intermediate Similarity	NPD7819	Suspended
0.7582	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7229	Phase 3
0.7569	Intermediate Similarity	NPD2796	Approved
0.7566	Intermediate Similarity	NPD7411	Suspended
0.7564	Intermediate Similarity	NPD5494	Approved
0.754	Intermediate Similarity	NPD968	Approved
0.7535	Intermediate Similarity	NPD6355	Discontinued
0.7534	Intermediate Similarity	NPD6674	Discontinued
0.7534	Intermediate Similarity	NPD1652	Phase 2
0.7534	Intermediate Similarity	NPD2800	Approved
0.7517	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2424	Discontinued
0.7464	Intermediate Similarity	NPD2797	Approved
0.7445	Intermediate Similarity	NPD6583	Phase 3
0.7445	Intermediate Similarity	NPD5327	Phase 3
0.7445	Intermediate Similarity	NPD6582	Phase 2
0.7436	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7157	Approved
0.7423	Intermediate Similarity	NPD6559	Discontinued
0.7422	Intermediate Similarity	NPD2684	Approved
0.7415	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5735	Approved
0.741	Intermediate Similarity	NPD6584	Phase 3
0.74	Intermediate Similarity	NPD2532	Approved
0.74	Intermediate Similarity	NPD2534	Approved
0.74	Intermediate Similarity	NPD2533	Approved
0.7391	Intermediate Similarity	NPD7228	Approved
0.7383	Intermediate Similarity	NPD6666	Approved
0.7383	Intermediate Similarity	NPD6667	Approved
0.7375	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7340	Approved
0.7361	Intermediate Similarity	NPD4097	Suspended
0.7357	Intermediate Similarity	NPD3018	Phase 2
0.7346	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5844	Phase 1
0.7344	Intermediate Similarity	NPD290	Approved
0.7343	Intermediate Similarity	NPD1240	Approved
0.7343	Intermediate Similarity	NPD2238	Phase 2
0.7343	Intermediate Similarity	NPD4140	Approved
0.7339	Intermediate Similarity	NPD3020	Approved
0.7333	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7041	Phase 2
0.7328	Intermediate Similarity	NPD5535	Approved
0.7328	Intermediate Similarity	NPD7843	Approved
0.7324	Intermediate Similarity	NPD6798	Discontinued
0.7324	Intermediate Similarity	NPD3268	Approved
0.731	Intermediate Similarity	NPD2200	Suspended
0.731	Intermediate Similarity	NPD7097	Phase 1
0.7296	Intermediate Similarity	NPD7199	Phase 2
0.729	Intermediate Similarity	NPD6801	Discontinued
0.7286	Intermediate Similarity	NPD3691	Phase 2
0.7286	Intermediate Similarity	NPD3690	Phase 2
0.7279	Intermediate Similarity	NPD5125	Phase 3
0.7279	Intermediate Similarity	NPD5763	Approved
0.7279	Intermediate Similarity	NPD5126	Approved
0.7279	Intermediate Similarity	NPD5762	Approved
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD1398	Phase 1
0.7267	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6166	Phase 2
0.7261	Intermediate Similarity	NPD3882	Suspended
0.726	Intermediate Similarity	NPD3748	Approved
0.726	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7741	Discontinued
0.7255	Intermediate Similarity	NPD1653	Approved
0.7248	Intermediate Similarity	NPD4535	Phase 3
0.7244	Intermediate Similarity	NPD2801	Approved
0.7244	Intermediate Similarity	NPD8455	Phase 2
0.7241	Intermediate Similarity	NPD2157	Approved
0.7241	Intermediate Similarity	NPD1607	Approved
0.7241	Intermediate Similarity	NPD6353	Approved
0.723	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7037	Approved
0.7226	Intermediate Similarity	NPD6072	Discontinued
0.7222	Intermediate Similarity	NPD3620	Phase 2
0.7222	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1511	Approved
0.7215	Intermediate Similarity	NPD3749	Approved
0.7211	Intermediate Similarity	NPD1551	Phase 2
0.7211	Intermediate Similarity	NPD2935	Discontinued
0.7205	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2983	Phase 2
0.7194	Intermediate Similarity	NPD2982	Phase 2
0.7178	Intermediate Similarity	NPD3818	Discontinued
0.7174	Intermediate Similarity	NPD3705	Approved
0.7153	Intermediate Similarity	NPD5846	Approved
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7153	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD6516	Phase 2
0.7143	Intermediate Similarity	NPD4108	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD5929	Approved
0.7133	Intermediate Similarity	NPD6331	Phase 2
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7124	Intermediate Similarity	NPD1512	Approved
0.7122	Intermediate Similarity	NPD2981	Phase 2
0.7122	Intermediate Similarity	NPD2231	Phase 2
0.7122	Intermediate Similarity	NPD1608	Approved
0.7122	Intermediate Similarity	NPD2235	Phase 2
0.7105	Intermediate Similarity	NPD6799	Approved
0.7103	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3496	Discontinued
0.7099	Intermediate Similarity	NPD5451	Approved
0.7097	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2860	Approved
0.7097	Intermediate Similarity	NPD2859	Approved
0.7097	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4476	Approved
0.7095	Intermediate Similarity	NPD4477	Approved
0.7092	Intermediate Similarity	NPD3094	Phase 2
0.7091	Intermediate Similarity	NPD7074	Phase 3
0.7089	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5691	Approved
0.708	Intermediate Similarity	NPD3445	Approved
0.708	Intermediate Similarity	NPD3443	Approved
0.708	Intermediate Similarity	NPD3444	Approved
0.7078	Intermediate Similarity	NPD920	Approved
0.7075	Intermediate Similarity	NPD7119	Phase 2
0.7075	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3685	Discontinued
0.7068	Intermediate Similarity	NPD821	Approved
0.7067	Intermediate Similarity	NPD1243	Approved
0.7059	Intermediate Similarity	NPD7019	Approved
0.7059	Intermediate Similarity	NPD7020	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