NPASS Compound

Structure

NPC476255 OpenBabel07101719252D 43 47 0 0 1 0 0 0 0 0999 V2000 -5.8813 -3.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1492 -3.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1888 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4568 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0489 2.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2668 0.9146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2832 1.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8246 0.0761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5155 -0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1492 -1.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0153 -1.6319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1492 -0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3228 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4568 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3195 2.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4823 1.8177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0224 -0.4771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3202 -0.7842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6851 -0.3956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4172 -0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0153 -2.6319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3228 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2118 1.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2832 0.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1774 -0.2637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4568 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2284 -0.3956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4568 -0.5274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6851 -0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0374 -0.7196 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2284 -0.3956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.5274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2284 -0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0808 0.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8464 -0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5374 0.8192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2284 -0.1319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4568 -1.5274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9153 1.0008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5512 0.3681 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 1.5374 0.8192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 35 1 0 0 0 0 9 35 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 21 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 22 2 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 23 2 0 0 0 0 16 36 1 0 0 0 0 17 27 2 0 0 0 0 18 25 1 0 0 0 0 18 30 1 0 0 0 0 19 28 2 0 0 0 0 19 29 1 0 0 0 0 20 24 2 0 0 0 0 20 41 1 0 0 0 0 25 17 1 1 0 0 0 25 34 1 0 0 0 0 26 29 2 0 0 0 0 26 33 1 0 0 0 0 27 32 1 0 0 0 0 28 31 1 0 0 0 0 28 38 1 0 0 0 0 29 41 1 0 0 0 0 30 35 1 0 0 0 0 30 37 1 1 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 32 39 2 0 0 0 0 33 42 1 0 0 0 0 34 36 1 0 0 0 0 34 40 2 0 0 0 0 35 43 1 0 0 0 0 36 37 1 1 0 0 0 36 43 1 0 0 0 0 37 27 1 6 0 0 0 37 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.33
Volume:	632.102
LogP:	9.013
LogD:	5.372
LogS:	-4.84
# Rotatable Bonds:	9
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	6.468
Fsp3:	0.514
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.797
MDCK Permeability:	2.0470664821914397e-05
Pgp-inhibitor:	0.562
Pgp-substrate:	0.816
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.674

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	88.53343963623047%
Volume Distribution (VD):	2.965
Pgp-substrate:	8.640301704406738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.751
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.494
CYP2D6-inhibitor:	0.572
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.754

ADMET: Excretion

Clearance (CL):	14.707
Half-life (T1/2):	0.011

ADMET: Toxicity

hERG Blockers:	0.949
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.583
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.275
Carcinogencity:	0.911
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC476255

Natural Product ID:	NPC476255
*Common Name:**	BIMUUWRNJBALEP-AWNOVZCOSA-N
IUPAC Name:	n.a.
Synonyms:	3-O-Geranylforbesione
Standard InCHIKey:	BIMUUWRNJBALEP-AWNOVZCOSA-N
Standard InCHI:	InChI=1S/C37H46O6/c1-21(2)11-10-12-24(7)20-41-29-19-28(38)31-32(39)27-17-25-18-30-35(8,9)43-36(34(25)40,16-15-23(5)6)37(27,30)42-33(31)26(29)14-13-22(3)4/h11,13,15,17,19-20,25,30,38H,10,12,14,16,18H2,1-9H3/b24-20+/t25-,30+,36+,37-/m1/s1
SMILES:	CC(=CCCC(=COC1=C(C2=C(C(=C1)O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C)CC=C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558747
PubChem CID:	45268895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4090.0	nM	PMID[448256]

☑ 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 NPC476255 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	417
0.1-0.2	1581
0.2-0.3	3134
0.3-0.4	7292
0.4-0.5	10656
0.5-0.6	5453
0.6-0.7	5763
0.7-0.8	6801
0.8-0.85	1472
0.85-0.9	72
0.9-0.95	30
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC94796
0.9747	High Similarity	NPC62444
0.9686	High Similarity	NPC193222
0.9679	High Similarity	NPC475107
0.9679	High Similarity	NPC286422
0.9679	High Similarity	NPC43490
0.9623	High Similarity	NPC476056
0.9568	High Similarity	NPC475080
0.9563	High Similarity	NPC223413
0.9497	High Similarity	NPC476931
0.9497	High Similarity	NPC131578
0.9437	High Similarity	NPC189689
0.9387	High Similarity	NPC169018
0.9387	High Similarity	NPC476159
0.9268	High Similarity	NPC118128
0.9264	High Similarity	NPC476216
0.9264	High Similarity	NPC55422
0.9264	High Similarity	NPC47634
0.9264	High Similarity	NPC63514
0.9264	High Similarity	NPC75141
0.9259	High Similarity	NPC475109
0.9217	High Similarity	NPC98943
0.9212	High Similarity	NPC476229
0.9212	High Similarity	NPC476139
0.9162	High Similarity	NPC233978
0.9157	High Similarity	NPC162248
0.9146	High Similarity	NPC41598
0.9146	High Similarity	NPC40089
0.9146	High Similarity	NPC476146
0.9146	High Similarity	NPC158329
0.913	High Similarity	NPC476929
0.9108	High Similarity	NPC476162
0.9096	High Similarity	NPC476152
0.9096	High Similarity	NPC476311
0.9091	High Similarity	NPC476196
0.9074	High Similarity	NPC475106
0.9062	High Similarity	NPC476930
0.9006	High Similarity	NPC125969
0.8994	High Similarity	NPC473607
0.8935	High Similarity	NPC476199
0.8935	High Similarity	NPC476210
0.8929	High Similarity	NPC475398
0.8922	High Similarity	NPC477529
0.8882	High Similarity	NPC473729
0.8876	High Similarity	NPC227275
0.8869	High Similarity	NPC469393
0.8862	High Similarity	NPC315306
0.8862	High Similarity	NPC313717
0.8848	High Similarity	NPC316262
0.8848	High Similarity	NPC314653
0.8827	High Similarity	NPC201127
0.8824	High Similarity	NPC5671
0.8812	High Similarity	NPC288534
0.8802	High Similarity	NPC54903
0.8802	High Similarity	NPC286074
0.8795	High Similarity	NPC85047
0.8795	High Similarity	NPC120857
0.8795	High Similarity	NPC17274
0.878	High Similarity	NPC103816
0.878	High Similarity	NPC61382
0.8765	High Similarity	NPC164427
0.8758	High Similarity	NPC209760
0.8758	High Similarity	NPC100134
0.872	High Similarity	NPC313368
0.8712	High Similarity	NPC474637
0.8704	High Similarity	NPC476169
0.8696	High Similarity	NPC477957
0.8696	High Similarity	NPC470353
0.8696	High Similarity	NPC210597
0.869	High Similarity	NPC102810
0.869	High Similarity	NPC20734
0.8683	High Similarity	NPC469394
0.8675	High Similarity	NPC472581
0.8675	High Similarity	NPC469395
0.8671	High Similarity	NPC470676
0.8671	High Similarity	NPC473132
0.8671	High Similarity	NPC473135
0.865	High Similarity	NPC470352
0.8647	High Similarity	NPC474276
0.8647	High Similarity	NPC73899
0.8647	High Similarity	NPC147363
0.8647	High Similarity	NPC17105
0.8642	High Similarity	NPC472799
0.8642	High Similarity	NPC236756
0.8642	High Similarity	NPC311579
0.8639	High Similarity	NPC193698
0.8634	High Similarity	NPC471229
0.8634	High Similarity	NPC472580
0.8631	High Similarity	NPC150131
0.8614	High Similarity	NPC219861
0.8606	High Similarity	NPC470810
0.8606	High Similarity	NPC172687
0.8599	High Similarity	NPC204469
0.8598	High Similarity	NPC161650
0.8596	High Similarity	NPC289244
0.8596	High Similarity	NPC245975
0.859	High Similarity	NPC477272
0.8589	High Similarity	NPC471116
0.8588	High Similarity	NPC91650
0.858	High Similarity	NPC275878
0.858	High Similarity	NPC152477
0.858	High Similarity	NPC473996
0.8571	High Similarity	NPC267117
0.8571	High Similarity	NPC235610
0.8571	High Similarity	NPC471115
0.8571	High Similarity	NPC29777
0.8563	High Similarity	NPC109180
0.8563	High Similarity	NPC8927
0.8563	High Similarity	NPC273959
0.8563	High Similarity	NPC474240
0.8563	High Similarity	NPC475656
0.8563	High Similarity	NPC475148
0.8562	High Similarity	NPC39195
0.8562	High Similarity	NPC145467
0.8554	High Similarity	NPC474351
0.8554	High Similarity	NPC117985
0.8554	High Similarity	NPC478134
0.8554	High Similarity	NPC475883
0.8553	High Similarity	NPC82534
0.8553	High Similarity	NPC329678
0.8553	High Similarity	NPC477955
0.8547	High Similarity	NPC469345
0.8545	High Similarity	NPC264932
0.8545	High Similarity	NPC311574
0.8538	High Similarity	NPC154986
0.8538	High Similarity	NPC471969
0.8537	High Similarity	NPC146636
0.8537	High Similarity	NPC470354
0.8537	High Similarity	NPC20530
0.8537	High Similarity	NPC215917
0.8537	High Similarity	NPC472050
0.8537	High Similarity	NPC10754
0.8535	High Similarity	NPC171870
0.8528	High Similarity	NPC469405
0.8528	High Similarity	NPC293286
0.8528	High Similarity	NPC192189
0.8528	High Similarity	NPC203080
0.8521	High Similarity	NPC470377
0.8521	High Similarity	NPC292233
0.8521	High Similarity	NPC471975
0.8521	High Similarity	NPC470374
0.8521	High Similarity	NPC126204
0.8521	High Similarity	NPC478059
0.8521	High Similarity	NPC478060
0.8521	High Similarity	NPC476459
0.8519	High Similarity	NPC305965
0.8519	High Similarity	NPC46882
0.8519	High Similarity	NPC178484
0.8519	High Similarity	NPC132990
0.8519	High Similarity	NPC472636
0.8519	High Similarity	NPC478148
0.8512	High Similarity	NPC475888
0.8512	High Similarity	NPC62261
0.8512	High Similarity	NPC473908
0.8509	High Similarity	NPC473016
0.8509	High Similarity	NPC277032
0.8506	High Similarity	NPC208069
0.8503	High Similarity	NPC211107
0.8503	High Similarity	NPC474150
0.8503	High Similarity	NPC474162
0.8503	High Similarity	NPC472402
0.85	High Similarity	NPC308200
0.85	High Similarity	NPC47388
0.85	High Similarity	NPC470670
0.85	High Similarity	NPC91902
0.85	High Similarity	NPC473133
0.8497	Intermediate Similarity	NPC246877
0.8497	Intermediate Similarity	NPC221820
0.8494	Intermediate Similarity	NPC299436
0.8494	Intermediate Similarity	NPC474287
0.8494	Intermediate Similarity	NPC195136
0.8494	Intermediate Similarity	NPC472618
0.8494	Intermediate Similarity	NPC243701
0.8494	Intermediate Similarity	NPC475886
0.8491	Intermediate Similarity	NPC470673
0.8491	Intermediate Similarity	NPC271288
0.8491	Intermediate Similarity	NPC117716
0.8491	Intermediate Similarity	NPC470674
0.8488	Intermediate Similarity	NPC86809
0.8488	Intermediate Similarity	NPC98667
0.8488	Intermediate Similarity	NPC294149
0.8488	Intermediate Similarity	NPC232412
0.8485	Intermediate Similarity	NPC272196
0.8485	Intermediate Similarity	NPC196448
0.8485	Intermediate Similarity	NPC281137
0.8485	Intermediate Similarity	NPC52889
0.8485	Intermediate Similarity	NPC65504
0.8485	Intermediate Similarity	NPC282390
0.8485	Intermediate Similarity	NPC210048
0.848	Intermediate Similarity	NPC121333
0.848	Intermediate Similarity	NPC472620
0.8476	Intermediate Similarity	NPC31018
0.8476	Intermediate Similarity	NPC207809
0.8476	Intermediate Similarity	NPC234485
0.8476	Intermediate Similarity	NPC477958
0.8476	Intermediate Similarity	NPC471456
0.8476	Intermediate Similarity	NPC217706
0.8476	Intermediate Similarity	NPC175192
0.8476	Intermediate Similarity	NPC255807
0.8476	Intermediate Similarity	NPC48579

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 NPC476255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	923
0.2-0.3	1772
0.3-0.4	2626
0.4-0.5	1977
0.5-0.6	982
0.6-0.7	352
0.7-0.8	151
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8589	High Similarity	NPD8443	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD3882	Suspended
0.8415	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7819	Suspended
0.8274	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7411	Suspended
0.815	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4380	Phase 2
0.8081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2800	Approved
0.8037	Intermediate Similarity	NPD2533	Approved
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD2534	Approved
0.8037	Intermediate Similarity	NPD2532	Approved
0.8024	Intermediate Similarity	NPD6801	Discontinued
0.8024	Intermediate Similarity	NPD1934	Approved
0.8012	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7977	Intermediate Similarity	NPD6166	Phase 2
0.7977	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6799	Approved
0.7941	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7889	Intermediate Similarity	NPD8434	Phase 2
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7874	Intermediate Similarity	NPD2403	Approved
0.787	Intermediate Similarity	NPD2801	Approved
0.7865	Intermediate Similarity	NPD7808	Phase 3
0.7836	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3817	Phase 2
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1510	Phase 2
0.7809	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1512	Approved
0.7764	Intermediate Similarity	NPD6099	Approved
0.7764	Intermediate Similarity	NPD2796	Approved
0.7764	Intermediate Similarity	NPD6100	Approved
0.7759	Intermediate Similarity	NPD6232	Discontinued
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.774	Intermediate Similarity	NPD5844	Phase 1
0.7709	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6651	Approved
0.7683	Intermediate Similarity	NPD3750	Approved
0.7673	Intermediate Similarity	NPD1240	Approved
0.7667	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1511	Approved
0.764	Intermediate Similarity	NPD7054	Approved
0.7637	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5403	Approved
0.7616	Intermediate Similarity	NPD5402	Approved
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD7472	Approved
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7557	Intermediate Similarity	NPD5711	Approved
0.7557	Intermediate Similarity	NPD5710	Approved
0.7529	Intermediate Similarity	NPD3226	Approved
0.7526	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD1465	Phase 2
0.7432	Intermediate Similarity	NPD8313	Approved
0.7432	Intermediate Similarity	NPD8312	Approved
0.7419	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7381	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3748	Approved
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.7329	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7435	Discontinued
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7698	Approved
0.7318	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2346	Discontinued
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7262	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4628	Phase 3
0.7257	Intermediate Similarity	NPD5761	Phase 2
0.7257	Intermediate Similarity	NPD5760	Phase 2
0.7255	Intermediate Similarity	NPD7907	Approved
0.7254	Intermediate Similarity	NPD6780	Approved
0.7254	Intermediate Similarity	NPD6781	Approved
0.7254	Intermediate Similarity	NPD6777	Approved
0.7254	Intermediate Similarity	NPD6776	Approved
0.7254	Intermediate Similarity	NPD6778	Approved
0.7254	Intermediate Similarity	NPD6782	Approved
0.7254	Intermediate Similarity	NPD6779	Approved
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7235	Intermediate Similarity	NPD7390	Discontinued
0.7229	Intermediate Similarity	NPD2935	Discontinued
0.7225	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD8151	Discontinued
0.7222	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2309	Approved
0.7215	Intermediate Similarity	NPD4749	Approved
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.72	Intermediate Similarity	NPD37	Approved
0.7198	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7228	Approved
0.7191	Intermediate Similarity	NPD6234	Discontinued
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7874	Approved
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7172	Intermediate Similarity	NPD7701	Phase 2
0.7169	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.715	Intermediate Similarity	NPD7801	Approved
0.7134	Intermediate Similarity	NPD943	Approved
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7199	Phase 2
0.711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8320	Phase 1
0.7107	Intermediate Similarity	NPD8319	Approved
0.7093	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD6355	Discontinued
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD4363	Phase 3
0.7083	Intermediate Similarity	NPD4360	Phase 2
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD4665	Approved
0.7062	Intermediate Similarity	NPD7699	Phase 2
0.7062	Intermediate Similarity	NPD7700	Phase 2
0.7055	Intermediate Similarity	NPD4625	Phase 3
0.7053	Intermediate Similarity	NPD4287	Approved
0.7047	Intermediate Similarity	NPD4361	Phase 2
0.7047	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6764	Approved
0.7043	Intermediate Similarity	NPD6765	Approved
0.703	Intermediate Similarity	NPD4060	Phase 1
0.7012	Intermediate Similarity	NPD2313	Discontinued
0.7012	Intermediate Similarity	NPD3268	Approved
0.7005	Intermediate Similarity	NPD3057	Approved
0.7005	Intermediate Similarity	NPD8366	Approved
0.7	Intermediate Similarity	NPD2654	Approved
0.6995	Remote Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD6534	Approved
0.6995	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD447	Suspended
0.6981	Remote Similarity	NPD1610	Phase 2
0.698	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7783	Phase 2
0.6977	Remote Similarity	NPD3300	Phase 2
0.6952	Remote Similarity	NPD7685	Pre-registration
0.695	Remote Similarity	NPD7584	Approved
0.6949	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2424	Discontinued
0.6939	Remote Similarity	NPD8285	Discontinued
0.6935	Remote Similarity	NPD1729	Discontinued
0.6923	Remote Similarity	NPD8127	Discontinued
0.6919	Remote Similarity	NPD3533	Approved
0.6919	Remote Similarity	NPD2972	Approved
0.6919	Remote Similarity	NPD6823	Phase 2
0.6909	Remote Similarity	NPD3764	Approved
0.6897	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6784	Approved
0.6895	Remote Similarity	NPD6785	Approved
0.689	Remote Similarity	NPD6832	Phase 2
0.6882	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8491	Approved
0.6871	Remote Similarity	NPD2798	Approved
0.6871	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD2493	Approved
0.6869	Remote Similarity	NPD2494	Approved
0.6864	Remote Similarity	NPD7033	Discontinued
0.6862	Remote Similarity	NPD7240	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