NPASS Compound

Structure

NPC68292 OpenBabel07101718322D 26 28 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 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 2.2321 -0.8660 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 1.7321 1.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 1 0 0 0 18 25 1 0 0 0 0 19 26 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 6 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.25
Volume:	390.65
LogP:	4.839
LogD:	3.912
LogS:	-4.485
# Rotatable Bonds:	3
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	4.345
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.696
MDCK Permeability:	1.6812644389574416e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	97.76573944091797%
Volume Distribution (VD):	2.175
Pgp-substrate:	2.5835869312286377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.681
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	0.364
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	4.505
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.297
Skin Sensitization:	0.846
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.098
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC68292

Natural Product ID:	NPC68292
*Common Name:**	Fortunin C
IUPAC Name:	(4bS,8aS,9R,10R)-3,10-dimethoxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-4,9-diol
Synonyms:	Fortunin C
Standard InCHIKey:	HSNPSWRYBNJNOF-ZJDLJICXSA-N
Standard InCHI:	InChI=1S/C22H34O4/c1-12(2)13-11-14-15(16(23)18(13)25-6)22(5)10-8-9-21(3,4)20(22)17(24)19(14)26-7/h11-12,17,19-20,23-24H,8-10H2,1-7H3/t17-,19+,20-,22+/m0/s1
SMILES:	CC(C)c1cc2c(c(c1OC)O)[C@@]1(C)CCCC(C)(C)[C@@H]1[C@H]([C@@H]2OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470291
PubChem CID:	24970401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	bark	n.a.	n.a.	PMID[18549276]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30638	Cryptomeria fortunei	Species	Cupressaceae	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
Others	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	58.5	%	PMID[459846]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	56.2	%	PMID[459846]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	14.4	%	PMID[459846]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	10.8	%	PMID[459846]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	9.3	%	PMID[459846]

☑ 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 NPC68292 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	416
0.1-0.2	1423
0.2-0.3	3393
0.3-0.4	8219
0.4-0.5	10556
0.5-0.6	5042
0.6-0.7	9450
0.7-0.8	3550
0.8-0.85	523
0.85-0.9	118
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC227719
0.9612	High Similarity	NPC312341
0.938	High Similarity	NPC201069
0.9154	High Similarity	NPC471077
0.9104	High Similarity	NPC311256
0.9098	High Similarity	NPC228843
0.9098	High Similarity	NPC59239
0.9085	High Similarity	NPC183380
0.8978	High Similarity	NPC114171
0.8978	High Similarity	NPC230124
0.8978	High Similarity	NPC184613
0.8978	High Similarity	NPC6300
0.8963	High Similarity	NPC471942
0.8947	High Similarity	NPC143483
0.8947	High Similarity	NPC99795
0.8939	High Similarity	NPC307050
0.8939	High Similarity	NPC472968
0.8939	High Similarity	NPC277458
0.8931	High Similarity	NPC470724
0.8929	High Similarity	NPC164183
0.8897	High Similarity	NPC475227
0.8897	High Similarity	NPC200645
0.8897	High Similarity	NPC106669
0.8889	High Similarity	NPC2745
0.8881	High Similarity	NPC78575
0.8828	High Similarity	NPC157783
0.8819	High Similarity	NPC195561
0.8819	High Similarity	NPC158784
0.8815	High Similarity	NPC321502
0.8811	High Similarity	NPC470757
0.8806	High Similarity	NPC470727
0.8794	High Similarity	NPC133251
0.8794	High Similarity	NPC473845
0.8777	High Similarity	NPC308768
0.8777	High Similarity	NPC12668
0.8768	High Similarity	NPC22902
0.8768	High Similarity	NPC242715
0.8768	High Similarity	NPC56329
0.8759	High Similarity	NPC313081
0.8759	High Similarity	NPC302915
0.8741	High Similarity	NPC58752
0.8722	High Similarity	NPC118533
0.8722	High Similarity	NPC21563
0.8722	High Similarity	NPC186889
0.8722	High Similarity	NPC165045
0.8712	High Similarity	NPC148627
0.8712	High Similarity	NPC29008
0.8712	High Similarity	NPC470726
0.8712	High Similarity	NPC266705
0.8712	High Similarity	NPC228771
0.8705	High Similarity	NPC105847
0.8705	High Similarity	NPC220344
0.8705	High Similarity	NPC243996
0.8705	High Similarity	NPC132804
0.8705	High Similarity	NPC275061
0.8705	High Similarity	NPC218131
0.8705	High Similarity	NPC243759
0.8699	High Similarity	NPC325860
0.8696	High Similarity	NPC30632
0.8696	High Similarity	NPC477939
0.8696	High Similarity	NPC54743
0.8696	High Similarity	NPC209985
0.8696	High Similarity	NPC177160
0.8696	High Similarity	NPC156502
0.8696	High Similarity	NPC29799
0.8696	High Similarity	NPC143139
0.8696	High Similarity	NPC202846
0.8696	High Similarity	NPC10737
0.8696	High Similarity	NPC263367
0.8686	High Similarity	NPC187616
0.8686	High Similarity	NPC193026
0.8686	High Similarity	NPC125649
0.8686	High Similarity	NPC209199
0.8686	High Similarity	NPC49603
0.8681	High Similarity	NPC473876
0.8681	High Similarity	NPC130959
0.8681	High Similarity	NPC179809
0.8681	High Similarity	NPC474940
0.8681	High Similarity	NPC303013
0.8681	High Similarity	NPC474795
0.8681	High Similarity	NPC212142
0.8681	High Similarity	NPC159697
0.8676	High Similarity	NPC14224
0.8676	High Similarity	NPC161958
0.8667	High Similarity	NPC196193
0.8652	High Similarity	NPC175838
0.8633	High Similarity	NPC3072
0.8633	High Similarity	NPC86605
0.8633	High Similarity	NPC200935
0.8633	High Similarity	NPC266453
0.8633	High Similarity	NPC266006
0.8633	High Similarity	NPC46277
0.8633	High Similarity	NPC151656
0.8633	High Similarity	NPC156948
0.8633	High Similarity	NPC230919
0.8633	High Similarity	NPC301765
0.8626	High Similarity	NPC471794
0.8623	High Similarity	NPC200557
0.8623	High Similarity	NPC158142
0.8623	High Similarity	NPC256262
0.8623	High Similarity	NPC10314
0.8623	High Similarity	NPC108198
0.8623	High Similarity	NPC294884
0.8623	High Similarity	NPC241241
0.8623	High Similarity	NPC69029
0.8621	High Similarity	NPC220006
0.8621	High Similarity	NPC181452
0.8613	High Similarity	NPC170185
0.8611	High Similarity	NPC474397
0.8601	High Similarity	NPC472457
0.8601	High Similarity	NPC286245
0.8601	High Similarity	NPC272619
0.8601	High Similarity	NPC90645
0.8592	High Similarity	NPC469630
0.8582	High Similarity	NPC5428
0.8582	High Similarity	NPC476536
0.8582	High Similarity	NPC265075
0.8582	High Similarity	NPC35216
0.8571	High Similarity	NPC471183
0.8571	High Similarity	NPC9067
0.8571	High Similarity	NPC29868
0.8571	High Similarity	NPC212942
0.8571	High Similarity	NPC79622
0.8562	High Similarity	NPC469706
0.8562	High Similarity	NPC145979
0.8562	High Similarity	NPC469707
0.8562	High Similarity	NPC225815
0.8562	High Similarity	NPC185955
0.8562	High Similarity	NPC214326
0.8562	High Similarity	NPC218041
0.8562	High Similarity	NPC260781
0.8562	High Similarity	NPC9933
0.8562	High Similarity	NPC182368
0.8561	High Similarity	NPC471693
0.8561	High Similarity	NPC133025
0.8561	High Similarity	NPC77861
0.8552	High Similarity	NPC290902
0.8552	High Similarity	NPC117788
0.8552	High Similarity	NPC474856
0.8552	High Similarity	NPC291326
0.8552	High Similarity	NPC474834
0.8551	High Similarity	NPC478085
0.8551	High Similarity	NPC160697
0.8542	High Similarity	NPC233980
0.8542	High Similarity	NPC112251
0.8542	High Similarity	NPC260397
0.854	High Similarity	NPC18842
0.854	High Similarity	NPC303144
0.8531	High Similarity	NPC473108
0.8531	High Similarity	NPC50250
0.8531	High Similarity	NPC471065
0.8531	High Similarity	NPC253015
0.8529	High Similarity	NPC242807
0.8529	High Similarity	NPC64201
0.8529	High Similarity	NPC187998
0.8529	High Similarity	NPC153739
0.8529	High Similarity	NPC257582
0.8529	High Similarity	NPC77040
0.8529	High Similarity	NPC145305
0.8529	High Similarity	NPC42300
0.8529	High Similarity	NPC174495
0.8529	High Similarity	NPC92164
0.8529	High Similarity	NPC241522
0.8521	High Similarity	NPC183709
0.8521	High Similarity	NPC186033
0.8521	High Similarity	NPC470917
0.8519	High Similarity	NPC252307
0.8519	High Similarity	NPC282703
0.8519	High Similarity	NPC45774
0.8519	High Similarity	NPC11258
0.8519	High Similarity	NPC245826
0.8519	High Similarity	NPC128208
0.8519	High Similarity	NPC129570
0.8519	High Similarity	NPC21867
0.8519	High Similarity	NPC474178
0.8519	High Similarity	NPC184733
0.8511	High Similarity	NPC73505
0.8511	High Similarity	NPC165026
0.8511	High Similarity	NPC34431
0.8511	High Similarity	NPC295719
0.8493	Intermediate Similarity	NPC474893
0.8493	Intermediate Similarity	NPC44452
0.8493	Intermediate Similarity	NPC475940
0.8485	Intermediate Similarity	NPC85488
0.8485	Intermediate Similarity	NPC152946
0.8478	Intermediate Similarity	NPC26394
0.8467	Intermediate Similarity	NPC15543
0.8467	Intermediate Similarity	NPC474017
0.8467	Intermediate Similarity	NPC277804
0.8462	Intermediate Similarity	NPC474104
0.8462	Intermediate Similarity	NPC469644
0.8456	Intermediate Similarity	NPC475875
0.8456	Intermediate Similarity	NPC62051
0.8451	Intermediate Similarity	NPC471414
0.8451	Intermediate Similarity	NPC472089
0.8451	Intermediate Similarity	NPC87725
0.8451	Intermediate Similarity	NPC263261
0.8446	Intermediate Similarity	NPC160196
0.8444	Intermediate Similarity	NPC106511
0.844	Intermediate Similarity	NPC32630

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 NPC68292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	836
0.2-0.3	1790
0.3-0.4	2750
0.4-0.5	1788
0.5-0.6	967
0.6-0.7	562
0.7-0.8	108
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD3619	Clinical (unspecified phase)
0.8815	High Similarity	NPD3620	Phase 2
0.8582	High Similarity	NPD6674	Discontinued
0.8321	Intermediate Similarity	NPD3027	Phase 3
0.8014	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1613	Approved
0.7971	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD5735	Approved
0.7945	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3657	Discovery
0.7826	Intermediate Similarity	NPD6696	Suspended
0.7826	Intermediate Similarity	NPD8651	Approved
0.7792	Intermediate Similarity	NPD37	Approved
0.7786	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.777	Intermediate Similarity	NPD3094	Phase 2
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD3092	Approved
0.773	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5283	Phase 1
0.771	Intermediate Similarity	NPD228	Approved
0.7682	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2861	Phase 2
0.7655	Intermediate Similarity	NPD4097	Suspended
0.7654	Intermediate Similarity	NPD7228	Approved
0.7643	Intermediate Similarity	NPD4966	Approved
0.7643	Intermediate Similarity	NPD4965	Approved
0.7643	Intermediate Similarity	NPD4967	Phase 2
0.7626	Intermediate Similarity	NPD5327	Phase 3
0.7622	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3705	Approved
0.7574	Intermediate Similarity	NPD3091	Approved
0.7568	Intermediate Similarity	NPD5763	Approved
0.7568	Intermediate Similarity	NPD5762	Approved
0.7552	Intermediate Similarity	NPD4625	Phase 3
0.7531	Intermediate Similarity	NPD2489	Approved
0.7531	Intermediate Similarity	NPD27	Approved
0.7517	Intermediate Similarity	NPD4140	Approved
0.7516	Intermediate Similarity	NPD3051	Approved
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7481	Intermediate Similarity	NPD7157	Approved
0.7469	Intermediate Similarity	NPD2970	Approved
0.7469	Intermediate Similarity	NPD2969	Approved
0.7465	Intermediate Similarity	NPD4624	Approved
0.7464	Intermediate Similarity	NPD4626	Approved
0.7453	Intermediate Similarity	NPD8127	Discontinued
0.745	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7340	Approved
0.7424	Intermediate Similarity	NPD3022	Approved
0.7424	Intermediate Similarity	NPD3021	Approved
0.7415	Intermediate Similarity	NPD6353	Approved
0.7407	Intermediate Similarity	NPD6232	Discontinued
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7391	Intermediate Similarity	NPD1357	Approved
0.7388	Intermediate Similarity	NPD7635	Approved
0.7381	Intermediate Similarity	NPD7313	Approved
0.7381	Intermediate Similarity	NPD7312	Approved
0.7381	Intermediate Similarity	NPD7310	Approved
0.7381	Intermediate Similarity	NPD7311	Approved
0.7376	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4749	Approved
0.7353	Intermediate Similarity	NPD4663	Approved
0.7338	Intermediate Similarity	NPD3095	Discontinued
0.7338	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7309	Approved
0.731	Intermediate Similarity	NPD7906	Approved
0.7303	Intermediate Similarity	NPD8166	Discontinued
0.7296	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD4578	Approved
0.7273	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7041	Phase 2
0.7267	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD6100	Approved
0.7266	Intermediate Similarity	NPD5691	Approved
0.7255	Intermediate Similarity	NPD2677	Approved
0.7234	Intermediate Similarity	NPD1610	Phase 2
0.7233	Intermediate Similarity	NPD1934	Approved
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7214	Intermediate Similarity	NPD5125	Phase 3
0.7214	Intermediate Similarity	NPD5126	Approved
0.7206	Intermediate Similarity	NPD1398	Phase 1
0.7194	Intermediate Similarity	NPD7741	Discontinued
0.7192	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD4110	Phase 3
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7172	Intermediate Similarity	NPD5736	Approved
0.7172	Intermediate Similarity	NPD3018	Phase 2
0.7162	Intermediate Similarity	NPD2238	Phase 2
0.716	Intermediate Similarity	NPD7833	Phase 2
0.716	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7831	Phase 2
0.716	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD2563	Approved
0.7143	Intermediate Similarity	NPD2342	Discontinued
0.7143	Intermediate Similarity	NPD7985	Registered
0.7143	Intermediate Similarity	NPD5241	Discontinued
0.7143	Intermediate Similarity	NPD2560	Approved
0.7134	Intermediate Similarity	NPD7199	Phase 2
0.7133	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4536	Approved
0.7133	Intermediate Similarity	NPD4538	Approved
0.7132	Intermediate Similarity	NPD7843	Approved
0.7124	Intermediate Similarity	NPD3060	Approved
0.7124	Intermediate Similarity	NPD5177	Phase 3
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6166	Phase 2
0.7101	Intermediate Similarity	NPD6671	Approved
0.7099	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6071	Discontinued
0.709	Intermediate Similarity	NPD2684	Approved
0.7089	Intermediate Similarity	NPD1653	Approved
0.7083	Intermediate Similarity	NPD1283	Approved
0.708	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6331	Phase 2
0.7073	Intermediate Similarity	NPD4666	Phase 3
0.7047	Intermediate Similarity	NPD1558	Phase 1
0.7044	Intermediate Similarity	NPD4005	Discontinued
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7027	Intermediate Similarity	NPD5111	Phase 2
0.7027	Intermediate Similarity	NPD5109	Approved
0.7027	Intermediate Similarity	NPD5110	Phase 2
0.7021	Intermediate Similarity	NPD1651	Approved
0.7014	Intermediate Similarity	NPD2983	Phase 2
0.7014	Intermediate Similarity	NPD2982	Phase 2
0.7013	Intermediate Similarity	NPD4237	Approved
0.7013	Intermediate Similarity	NPD4236	Phase 3
0.7012	Intermediate Similarity	NPD5709	Phase 3
0.7006	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD1091	Approved
0.698	Remote Similarity	NPD6663	Approved
0.6975	Remote Similarity	NPD2801	Approved
0.6975	Remote Similarity	NPD5929	Approved
0.6975	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5960	Phase 3
0.6974	Remote Similarity	NPD5588	Approved
0.6972	Remote Similarity	NPD3019	Approved
0.6972	Remote Similarity	NPD4059	Approved
0.6962	Remote Similarity	NPD6090	Discontinued
0.6957	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1548	Phase 1
0.6946	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2232	Approved
0.6944	Remote Similarity	NPD2233	Approved
0.6944	Remote Similarity	NPD2230	Approved
0.6944	Remote Similarity	NPD2981	Phase 2
0.6943	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7074	Phase 3
0.6936	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2979	Phase 3
0.6932	Remote Similarity	NPD2490	Approved
0.6932	Remote Similarity	NPD2488	Approved
0.6928	Remote Similarity	NPD2438	Suspended
0.6928	Remote Similarity	NPD6959	Discontinued
0.6913	Remote Similarity	NPD6798	Discontinued
0.6912	Remote Similarity	NPD4750	Phase 3
0.6908	Remote Similarity	NPD6111	Discontinued
0.6908	Remote Similarity	NPD6896	Approved
0.6908	Remote Similarity	NPD6895	Approved
0.6908	Remote Similarity	NPD7097	Phase 1
0.6905	Remote Similarity	NPD4481	Phase 3
0.6899	Remote Similarity	NPD2532	Approved
0.6899	Remote Similarity	NPD2534	Approved
0.6899	Remote Similarity	NPD1809	Phase 2
0.6899	Remote Similarity	NPD3645	Discontinued
0.6899	Remote Similarity	NPD2533	Approved
0.6894	Remote Similarity	NPD7028	Phase 2
0.6894	Remote Similarity	NPD4380	Phase 2
0.689	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD290	Approved
0.6887	Remote Similarity	NPD5124	Phase 1
0.6887	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7054	Approved
0.6879	Remote Similarity	NPD8313	Approved
0.6879	Remote Similarity	NPD5058	Phase 3
0.6879	Remote Similarity	NPD7124	Phase 2
0.6879	Remote Similarity	NPD5536	Phase 2
0.6879	Remote Similarity	NPD8312	Approved
0.6875	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD1611	Approved
0.6871	Remote Similarity	NPD2977	Approved
0.6871	Remote Similarity	NPD8455	Phase 2
0.6871	Remote Similarity	NPD6584	Phase 3
0.6871	Remote Similarity	NPD2978	Approved
0.6867	Remote Similarity	NPD2674	Phase 3
0.6867	Remote Similarity	NPD8032	Phase 2

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