NPASS Compound

Structure

NPC163036 OpenBabel07101718232D 39 40 0 0 1 0 0 0 0 0999 V2000 4.3301 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8301 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3301 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -0.4019 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 0 0 0 0 0 0 0 0 0 0 -5.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 0.4641 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -2.1340 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 3.8301 -2.3660 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 -2.2321 -2.1340 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 1.3301 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -1.2679 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 -4.7321 0.4641 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2321 1.3301 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 10 2 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 9 35 1 0 0 0 0 10 36 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 28 2 0 0 0 0 13 17 1 0 0 0 0 13 29 2 0 0 0 0 14 18 2 0 0 0 0 14 29 1 0 0 0 0 15 19 1 0 0 0 0 15 30 2 0 0 0 0 16 20 2 0 0 0 0 16 30 1 0 0 0 0 17 31 2 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 20 32 1 0 0 0 0 21 25 2 0 0 0 0 21 30 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 33 1 0 0 0 0 24 35 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 36 1 0 0 0 0 31 37 1 0 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 33 38 1 6 0 0 0 34 39 1 0 0 0 0 35 7 1 1 0 0 0 36 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.36
Volume:	611.469
LogP:	8.126
LogD:	5.389
LogS:	-2.942
# Rotatable Bonds:	15
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	4.498
Fsp3:	0.389
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	1.8200355043518357e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.302

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	102.85724639892578%
Volume Distribution (VD):	1.062
Pgp-substrate:	3.0791373252868652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.257
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.757
CYP2C19-substrate:	0.202
CYP2C9-inhibitor:	0.766
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.977
CYP3A4-substrate:	0.761

ADMET: Excretion

Clearance (CL):	6.655
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.965
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.956
Carcinogencity:	0.217
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.233

Download Data

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

Natural Product: NPC163036

Natural Product ID:	NPC163036
*Common Name:**	(12's)-Bisbakuchiol C
IUPAC Name:	4-[(E,3S,6S)-3-ethenyl-7-[4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenoxy]-6-hydroxy-3,7-dimethyloct-1-enyl]phenol
Synonyms:	(12'S)-Bisbakuchiol C
Standard InCHIKey:	HBUHJZOOZIOPLC-GOBFGHSLSA-N
Standard InCHI:	InChI=1S/C36H48O3/c1-9-35(7,24-11-12-28(3)4)25-21-30-15-19-32(20-16-30)39-34(5,6)33(38)23-27-36(8,10-2)26-22-29-13-17-31(37)18-14-29/h9-10,12-22,25-26,33,37-38H,1-2,11,23-24,27H2,3-8H3/b25-21+,26-22+/t33-,35+,36-/m0/s1
SMILES:	C=C[C@@](/C=C/c1ccc(cc1)O)(CC[C@@H](C(Oc1ccc(cc1)/C=C/[C@@](CCC=C(C)C)(C=C)C)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258478
PubChem CID:	44450330
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	2
Others	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[547796]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[547796]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[547796]
NPT2	Others	Unspecified		IC50	=	12200.0	nM	PMID[547796]

☑ 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 NPC163036 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	295
0.1-0.2	1383
0.2-0.3	4121
0.3-0.4	12014
0.4-0.5	6745
0.5-0.6	6604
0.6-0.7	8931
0.7-0.8	2414
0.8-0.85	180
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.885	High Similarity	NPC46844
0.875	High Similarity	NPC127389
0.875	High Similarity	NPC290451
0.8559	High Similarity	NPC192596
0.8537	High Similarity	NPC48990
0.8537	High Similarity	NPC293701
0.8537	High Similarity	NPC114901
0.8512	High Similarity	NPC207613
0.8509	High Similarity	NPC201959
0.8496	Intermediate Similarity	NPC113457
0.8468	Intermediate Similarity	NPC471578
0.8468	Intermediate Similarity	NPC101025
0.8468	Intermediate Similarity	NPC194519
0.8468	Intermediate Similarity	NPC51633
0.8443	Intermediate Similarity	NPC312675
0.8443	Intermediate Similarity	NPC473853
0.8443	Intermediate Similarity	NPC262156
0.8443	Intermediate Similarity	NPC184651
0.8443	Intermediate Similarity	NPC324571
0.8443	Intermediate Similarity	NPC54872
0.8443	Intermediate Similarity	NPC113865
0.8443	Intermediate Similarity	NPC343720
0.8443	Intermediate Similarity	NPC470212
0.8435	Intermediate Similarity	NPC474272
0.8407	Intermediate Similarity	NPC470393
0.84	Intermediate Similarity	NPC191037
0.84	Intermediate Similarity	NPC58607
0.84	Intermediate Similarity	NPC178284
0.8387	Intermediate Similarity	NPC94276
0.8387	Intermediate Similarity	NPC109822
0.8376	Intermediate Similarity	NPC165646
0.8374	Intermediate Similarity	NPC71090
0.8348	Intermediate Similarity	NPC75440
0.8347	Intermediate Similarity	NPC474320
0.8333	Intermediate Similarity	NPC86947
0.8333	Intermediate Similarity	NPC163332
0.8333	Intermediate Similarity	NPC135464
0.8333	Intermediate Similarity	NPC292056
0.8333	Intermediate Similarity	NPC147821
0.8333	Intermediate Similarity	NPC41706
0.8333	Intermediate Similarity	NPC92623
0.8333	Intermediate Similarity	NPC183181
0.8333	Intermediate Similarity	NPC319625
0.8333	Intermediate Similarity	NPC118787
0.8333	Intermediate Similarity	NPC164386
0.8333	Intermediate Similarity	NPC111247
0.8319	Intermediate Similarity	NPC474603
0.8319	Intermediate Similarity	NPC108875
0.8319	Intermediate Similarity	NPC38079
0.8319	Intermediate Similarity	NPC12987
0.8306	Intermediate Similarity	NPC471693
0.8306	Intermediate Similarity	NPC474130
0.8291	Intermediate Similarity	NPC55300
0.8291	Intermediate Similarity	NPC266932
0.8288	Intermediate Similarity	NPC471576
0.8268	Intermediate Similarity	NPC87224
0.8268	Intermediate Similarity	NPC222572
0.8264	Intermediate Similarity	NPC470626
0.8264	Intermediate Similarity	NPC474214
0.8261	Intermediate Similarity	NPC194034
0.825	Intermediate Similarity	NPC154256
0.825	Intermediate Similarity	NPC290470
0.8246	Intermediate Similarity	NPC154899
0.8246	Intermediate Similarity	NPC233396
0.824	Intermediate Similarity	NPC74478
0.823	Intermediate Similarity	NPC62351
0.8226	Intermediate Similarity	NPC150026
0.8226	Intermediate Similarity	NPC46586
0.8226	Intermediate Similarity	NPC204535
0.8226	Intermediate Similarity	NPC85488
0.8217	Intermediate Similarity	NPC103799
0.8211	Intermediate Similarity	NPC473875
0.8203	Intermediate Similarity	NPC86030
0.8203	Intermediate Similarity	NPC5851
0.8197	Intermediate Similarity	NPC310338
0.8197	Intermediate Similarity	NPC281298
0.8197	Intermediate Similarity	NPC311595
0.8197	Intermediate Similarity	NPC24474
0.8182	Intermediate Similarity	NPC293619
0.8175	Intermediate Similarity	NPC81641
0.8175	Intermediate Similarity	NPC148627
0.816	Intermediate Similarity	NPC317769
0.816	Intermediate Similarity	NPC31344
0.816	Intermediate Similarity	NPC261992
0.816	Intermediate Similarity	NPC280704
0.816	Intermediate Similarity	NPC474160
0.8154	Intermediate Similarity	NPC470752
0.8151	Intermediate Similarity	NPC301735
0.8151	Intermediate Similarity	NPC35344
0.8151	Intermediate Similarity	NPC141003
0.814	Intermediate Similarity	NPC472338
0.8136	Intermediate Similarity	NPC139617
0.8136	Intermediate Similarity	NPC78918
0.813	Intermediate Similarity	NPC95614
0.813	Intermediate Similarity	NPC232295
0.813	Intermediate Similarity	NPC242885
0.813	Intermediate Similarity	NPC56214
0.813	Intermediate Similarity	NPC227217
0.813	Intermediate Similarity	NPC117780
0.813	Intermediate Similarity	NPC165133
0.813	Intermediate Similarity	NPC232316
0.8125	Intermediate Similarity	NPC252307
0.8125	Intermediate Similarity	NPC474178
0.8125	Intermediate Similarity	NPC72529
0.8125	Intermediate Similarity	NPC245826
0.8115	Intermediate Similarity	NPC474040
0.811	Intermediate Similarity	NPC17837
0.811	Intermediate Similarity	NPC304630
0.8106	Intermediate Similarity	NPC93783
0.8103	Intermediate Similarity	NPC251306
0.8099	Intermediate Similarity	NPC473556
0.8099	Intermediate Similarity	NPC301651
0.8092	Intermediate Similarity	NPC475840
0.8087	Intermediate Similarity	NPC8302
0.8083	Intermediate Similarity	NPC161696
0.808	Intermediate Similarity	NPC36016
0.808	Intermediate Similarity	NPC188997
0.808	Intermediate Similarity	NPC100099
0.8077	Intermediate Similarity	NPC277804
0.8077	Intermediate Similarity	NPC162801
0.8077	Intermediate Similarity	NPC472597
0.8077	Intermediate Similarity	NPC30043
0.8077	Intermediate Similarity	NPC309787
0.8077	Intermediate Similarity	NPC469625
0.8077	Intermediate Similarity	NPC469613
0.8067	Intermediate Similarity	NPC115379
0.8062	Intermediate Similarity	NPC470258
0.8062	Intermediate Similarity	NPC218856
0.8062	Intermediate Similarity	NPC210623
0.8062	Intermediate Similarity	NPC3439
0.8062	Intermediate Similarity	NPC285339
0.8062	Intermediate Similarity	NPC475875
0.8062	Intermediate Similarity	NPC273295
0.8062	Intermediate Similarity	NPC222004
0.8062	Intermediate Similarity	NPC202582
0.8062	Intermediate Similarity	NPC190629
0.8062	Intermediate Similarity	NPC226788
0.8049	Intermediate Similarity	NPC32152
0.8047	Intermediate Similarity	NPC118533
0.8047	Intermediate Similarity	NPC5428
0.8047	Intermediate Similarity	NPC474119
0.8047	Intermediate Similarity	NPC165045
0.8047	Intermediate Similarity	NPC473993
0.8045	Intermediate Similarity	NPC77861
0.8031	Intermediate Similarity	NPC167571
0.8031	Intermediate Similarity	NPC278552
0.8031	Intermediate Similarity	NPC87113
0.8031	Intermediate Similarity	NPC207179
0.803	Intermediate Similarity	NPC478085
0.803	Intermediate Similarity	NPC117048
0.803	Intermediate Similarity	NPC124085
0.803	Intermediate Similarity	NPC184269
0.8016	Intermediate Similarity	NPC38761
0.8016	Intermediate Similarity	NPC76465
0.8015	Intermediate Similarity	NPC160991
0.8015	Intermediate Similarity	NPC16208
0.8015	Intermediate Similarity	NPC7903
0.8015	Intermediate Similarity	NPC184447
0.8015	Intermediate Similarity	NPC35932
0.8	Intermediate Similarity	NPC42300
0.8	Intermediate Similarity	NPC257582
0.8	Intermediate Similarity	NPC242807
0.8	Intermediate Similarity	NPC153739
0.8	Intermediate Similarity	NPC145305
0.8	Intermediate Similarity	NPC38996
0.8	Intermediate Similarity	NPC77040
0.8	Intermediate Similarity	NPC469612
0.8	Intermediate Similarity	NPC176730
0.8	Intermediate Similarity	NPC241522
0.8	Intermediate Similarity	NPC64201
0.8	Intermediate Similarity	NPC187998
0.8	Intermediate Similarity	NPC123175
0.8	Intermediate Similarity	NPC174495
0.8	Intermediate Similarity	NPC469614
0.8	Intermediate Similarity	NPC92164
0.8	Intermediate Similarity	NPC160380
0.7984	Intermediate Similarity	NPC184733
0.7984	Intermediate Similarity	NPC470213
0.7984	Intermediate Similarity	NPC129570
0.7984	Intermediate Similarity	NPC474131
0.7984	Intermediate Similarity	NPC45774
0.7984	Intermediate Similarity	NPC98631
0.7984	Intermediate Similarity	NPC11258
0.7984	Intermediate Similarity	NPC282703
0.7984	Intermediate Similarity	NPC21867
0.7984	Intermediate Similarity	NPC226661
0.7984	Intermediate Similarity	NPC274717
0.7984	Intermediate Similarity	NPC206615
0.7984	Intermediate Similarity	NPC470084
0.7984	Intermediate Similarity	NPC186843
0.7984	Intermediate Similarity	NPC128208
0.797	Intermediate Similarity	NPC61946
0.797	Intermediate Similarity	NPC151224
0.797	Intermediate Similarity	NPC164787
0.7969	Intermediate Similarity	NPC276212
0.7967	Intermediate Similarity	NPC283616
0.7966	Intermediate Similarity	NPC306045
0.7966	Intermediate Similarity	NPC7097
0.7966	Intermediate Similarity	NPC265211
0.7966	Intermediate Similarity	NPC36108

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 NPC163036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	874
0.2-0.3	1635
0.3-0.4	2684
0.4-0.5	1794
0.5-0.6	1072
0.6-0.7	674
0.7-0.8	134
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8793	High Similarity	NPD7157	Approved
0.8696	High Similarity	NPD7843	Approved
0.8673	High Similarity	NPD2684	Approved
0.8261	Intermediate Similarity	NPD290	Approved
0.8174	Intermediate Similarity	NPD968	Approved
0.813	Intermediate Similarity	NPD6516	Phase 2
0.813	Intermediate Similarity	NPD5846	Approved
0.8095	Intermediate Similarity	NPD8651	Approved
0.8062	Intermediate Similarity	NPD7095	Approved
0.8017	Intermediate Similarity	NPD6671	Approved
0.7955	Intermediate Similarity	NPD5735	Approved
0.7923	Intermediate Similarity	NPD3027	Phase 3
0.7903	Intermediate Similarity	NPD1357	Approved
0.7879	Intermediate Similarity	NPD4060	Phase 1
0.7874	Intermediate Similarity	NPD6582	Phase 2
0.7874	Intermediate Similarity	NPD6583	Phase 3
0.7833	Intermediate Similarity	NPD228	Approved
0.7829	Intermediate Similarity	NPD6584	Phase 3
0.782	Intermediate Similarity	NPD6355	Discontinued
0.7769	Intermediate Similarity	NPD2861	Phase 2
0.7754	Intermediate Similarity	NPD4628	Phase 3
0.7744	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3620	Phase 2
0.7744	Intermediate Similarity	NPD1613	Approved
0.7734	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD5327	Phase 3
0.7727	Intermediate Similarity	NPD6798	Discontinued
0.7717	Intermediate Similarity	NPD1610	Phase 2
0.771	Intermediate Similarity	NPD4908	Phase 1
0.7705	Intermediate Similarity	NPD5283	Phase 1
0.7704	Intermediate Similarity	NPD4536	Approved
0.7704	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD4538	Approved
0.7699	Intermediate Similarity	NPD2859	Approved
0.7699	Intermediate Similarity	NPD2860	Approved
0.768	Intermediate Similarity	NPD1548	Phase 1
0.7658	Intermediate Similarity	NPD9365	Approved
0.7652	Intermediate Similarity	NPD3020	Approved
0.763	Intermediate Similarity	NPD6353	Approved
0.7623	Intermediate Similarity	NPD821	Approved
0.7623	Intermediate Similarity	NPD5535	Approved
0.7612	Intermediate Similarity	NPD4140	Approved
0.7611	Intermediate Similarity	NPD2933	Approved
0.7611	Intermediate Similarity	NPD2934	Approved
0.7609	Intermediate Similarity	NPD4534	Discontinued
0.7594	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1091	Approved
0.7537	Intermediate Similarity	NPD4062	Phase 3
0.7537	Intermediate Similarity	NPD6233	Phase 2
0.7521	Intermediate Similarity	NPD5451	Approved
0.7521	Intermediate Similarity	NPD291	Approved
0.752	Intermediate Similarity	NPD3596	Phase 2
0.7519	Intermediate Similarity	NPD2231	Phase 2
0.7519	Intermediate Similarity	NPD2235	Phase 2
0.7518	Intermediate Similarity	NPD5588	Approved
0.7518	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD1358	Approved
0.748	Intermediate Similarity	NPD5585	Approved
0.748	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3685	Discontinued
0.7462	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7097	Phase 1
0.7444	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2667	Approved
0.7422	Intermediate Similarity	NPD2668	Approved
0.7417	Intermediate Similarity	NPD3134	Approved
0.7402	Intermediate Similarity	NPD1894	Discontinued
0.7402	Intermediate Similarity	NPD6581	Approved
0.7402	Intermediate Similarity	NPD6580	Approved
0.7394	Intermediate Similarity	NPD5058	Phase 3
0.7377	Intermediate Similarity	NPD3021	Approved
0.7377	Intermediate Similarity	NPD3022	Approved
0.7376	Intermediate Similarity	NPD4535	Phase 3
0.7372	Intermediate Similarity	NPD3052	Approved
0.7372	Intermediate Similarity	NPD3054	Approved
0.7368	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2424	Discontinued
0.7353	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1817	Approved
0.7348	Intermediate Similarity	NPD1819	Approved
0.7348	Intermediate Similarity	NPD1820	Approved
0.7348	Intermediate Similarity	NPD1818	Approved
0.7323	Intermediate Similarity	NPD5536	Phase 2
0.7313	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3092	Approved
0.7305	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2557	Approved
0.7293	Intermediate Similarity	NPD3691	Phase 2
0.7293	Intermediate Similarity	NPD3690	Phase 2
0.7293	Intermediate Similarity	NPD4624	Approved
0.7287	Intermediate Similarity	NPD1778	Approved
0.7286	Intermediate Similarity	NPD5763	Approved
0.7286	Intermediate Similarity	NPD5762	Approved
0.7279	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7266	Intermediate Similarity	NPD1182	Approved
0.7266	Intermediate Similarity	NPD3091	Approved
0.7259	Intermediate Similarity	NPD3164	Approved
0.7259	Intermediate Similarity	NPD3166	Approved
0.7259	Intermediate Similarity	NPD3180	Approved
0.7259	Intermediate Similarity	NPD3165	Approved
0.7259	Intermediate Similarity	NPD4625	Phase 3
0.7259	Intermediate Similarity	NPD3179	Approved
0.7259	Intermediate Similarity	NPD3167	Approved
0.7254	Intermediate Similarity	NPD4110	Phase 3
0.7254	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6653	Approved
0.7239	Intermediate Similarity	NPD4993	Discontinued
0.7234	Intermediate Similarity	NPD5958	Discontinued
0.7231	Intermediate Similarity	NPD3496	Discontinued
0.7231	Intermediate Similarity	NPD3847	Discontinued
0.723	Intermediate Similarity	NPD6072	Discontinued
0.7226	Intermediate Similarity	NPD1558	Phase 1
0.7218	Intermediate Similarity	NPD987	Approved
0.7209	Intermediate Similarity	NPD3443	Approved
0.7209	Intermediate Similarity	NPD3444	Approved
0.7209	Intermediate Similarity	NPD3445	Approved
0.7206	Intermediate Similarity	NPD7294	Phase 1
0.7206	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4359	Approved
0.7197	Intermediate Similarity	NPD4749	Approved
0.7183	Intermediate Similarity	NPD4162	Approved
0.7176	Intermediate Similarity	NPD1535	Discovery
0.7174	Intermediate Similarity	NPD4340	Discontinued
0.7172	Intermediate Similarity	NPD3536	Discontinued
0.7164	Intermediate Similarity	NPD5647	Approved
0.7164	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD1423	Approved
0.7143	Intermediate Similarity	NPD2156	Approved
0.7143	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD2155	Approved
0.7143	Intermediate Similarity	NPD2154	Approved
0.7133	Intermediate Similarity	NPD6331	Phase 2
0.7132	Intermediate Similarity	NPD5163	Phase 2
0.7132	Intermediate Similarity	NPD6179	Discontinued
0.7121	Intermediate Similarity	NPD1481	Phase 2
0.7121	Intermediate Similarity	NPD2232	Approved
0.7121	Intermediate Similarity	NPD2230	Approved
0.7121	Intermediate Similarity	NPD2233	Approved
0.7117	Intermediate Similarity	NPD111	Approved
0.7101	Intermediate Similarity	NPD2238	Phase 2
0.7092	Intermediate Similarity	NPD6032	Approved
0.709	Intermediate Similarity	NPD3094	Phase 2
0.709	Intermediate Similarity	NPD1794	Approved
0.709	Intermediate Similarity	NPD2797	Approved
0.7077	Intermediate Similarity	NPD3049	Approved
0.7077	Intermediate Similarity	NPD6382	Discontinued
0.7073	Intermediate Similarity	NPD9552	Approved
0.7068	Intermediate Similarity	NPD6540	Phase 3
0.7068	Intermediate Similarity	NPD6542	Approved
0.7068	Intermediate Similarity	NPD6543	Approved
0.7068	Intermediate Similarity	NPD2982	Phase 2
0.7068	Intermediate Similarity	NPD2429	Approved
0.7068	Intermediate Similarity	NPD2983	Phase 2
0.7068	Intermediate Similarity	NPD6539	Approved
0.7068	Intermediate Similarity	NPD2428	Approved
0.7063	Intermediate Similarity	NPD5062	Approved
0.7063	Intermediate Similarity	NPD3060	Approved
0.7063	Intermediate Similarity	NPD5061	Approved
0.7055	Intermediate Similarity	NPD3985	Discontinued
0.7045	Intermediate Similarity	NPD776	Approved
0.7045	Intermediate Similarity	NPD422	Phase 1
0.7034	Intermediate Similarity	NPD6666	Approved
0.7034	Intermediate Similarity	NPD6815	Approved
0.7034	Intermediate Similarity	NPD6667	Approved
0.7031	Intermediate Similarity	NPD4198	Discontinued
0.7029	Intermediate Similarity	NPD7477	Discontinued
0.7029	Intermediate Similarity	NPD3163	Approved
0.7029	Intermediate Similarity	NPD3162	Approved
0.7029	Intermediate Similarity	NPD7265	Discontinued
0.7029	Intermediate Similarity	NPD8032	Phase 2
0.7023	Intermediate Similarity	NPD4626	Approved
0.7023	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2554	Approved
0.7023	Intermediate Similarity	NPD2556	Approved
0.7018	Intermediate Similarity	NPD9295	Approved
0.7015	Intermediate Similarity	NPD6538	Approved
0.7015	Intermediate Similarity	NPD6541	Approved
0.7007	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD1242	Phase 1
0.7	Intermediate Similarity	NPD7741	Discontinued
0.7	Intermediate Similarity	NPD6677	Suspended
0.6993	Remote Similarity	NPD7833	Phase 2
0.6993	Remote Similarity	NPD7831	Phase 2
0.6993	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7037	Approved
0.6992	Remote Similarity	NPD2981	Phase 2
0.6992	Remote Similarity	NPD3972	Approved
0.6992	Remote Similarity	NPD1608	Approved
0.6992	Remote Similarity	NPD1840	Phase 2
0.6985	Remote Similarity	NPD5736	Approved
0.6985	Remote Similarity	NPD9494	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