NPASS Compound

Structure

CID219232 OpenBabel06191716012D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.5731 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 1.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 3.4641 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 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 -0.8660 -0.5000 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 5.1962 -2.0000 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 4.3301 -1.5000 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 2.5981 -0.5000 0.0000 C 0 0 1 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 3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 C 0 0 2 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 16 2 0 0 0 0 7 9 1 0 0 0 0 7 17 2 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 6 0 0 0 19 24 1 6 0 0 0 20 23 1 1 0 0 0 21 22 1 0 0 0 0 21 24 1 6 0 0 0 23 3 1 6 0 0 0 24 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.26
Volume:	396.469
LogP:	5.255
LogD:	4.294
LogS:	-5.581
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	4.726
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.613
MDCK Permeability:	1.7519307220936753e-05
Pgp-inhibitor:	0.577
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	70.19023895263672%
Volume Distribution (VD):	2.614
Pgp-substrate:	12.771219253540039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.375
CYP3A4-inhibitor:	0.889
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	7.395
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.947
Carcinogencity:	0.288
Eye Corrosion:	0.986
Eye Irritation:	0.907
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC219232

Natural Product ID:	NPC219232
*Common Name:**	Mooloolabene B
IUPAC Name:	(1S,4aR,6aS,10aS,10bR,12aS)-7,7,10a,12a-tetramethyl-4,4a,6,6a,8,9,10,10b,11,12-decahydro-1H-chrysene-1,2-dicarbaldehyde
Synonyms:
Standard InCHIKey:	ZUQQZYOCHBYEJX-AIGJZXDYSA-N
Standard InCHI:	InChI=1S/C24H34O2/c1-22(2)11-5-12-24(4)19-10-13-23(3)18(17(19)7-9-21(22)24)8-6-16(14-25)20(23)15-26/h6-7,14-15,18-21H,5,8-13H2,1-4H3/t18-,19-,20+,21-,23-,24+/m0/s1
SMILES:	CC1(C)CCC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC=C(C=O)[C@H]4C=O)C3=CC[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472502
PubChem CID:	11994180
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
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	Inner Gneerings, a group of shoals off Mooloolaba (Australia)	2005-JUL	PMID[17125226]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21608987]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7153777]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19735	Euonymus pellucidifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17690	Sideritis sventenii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18198	Selaginella willdenowii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19439	Calea zacatechichi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21265	Teucrium webbianum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19595	Lathyrus chloranthus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16397	Didymocarpus oblonga	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	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
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.2	ug.mL-1	PMID[474096]

☑ 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 NPC219232 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	228
0.1-0.2	2159
0.2-0.3	11213
0.3-0.4	14511
0.4-0.5	7722
0.5-0.6	4900
0.6-0.7	1693
0.7-0.8	236
0.8-0.85	22
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC128346
0.971	High Similarity	NPC211641
0.9178	High Similarity	NPC115515
0.9118	High Similarity	NPC4370
0.9118	High Similarity	NPC290350
0.8714	High Similarity	NPC155198
0.8684	High Similarity	NPC474509
0.8676	High Similarity	NPC52449
0.8676	High Similarity	NPC169275
0.8611	High Similarity	NPC474562
0.8608	High Similarity	NPC2709
0.859	High Similarity	NPC307258
0.8571	High Similarity	NPC193770
0.8553	High Similarity	NPC170793
0.8553	High Similarity	NPC90965
0.8451	Intermediate Similarity	NPC188292
0.8451	Intermediate Similarity	NPC260474
0.8356	Intermediate Similarity	NPC190035
0.8243	Intermediate Similarity	NPC303613
0.8243	Intermediate Similarity	NPC474228
0.8219	Intermediate Similarity	NPC2634
0.8219	Intermediate Similarity	NPC265782
0.8219	Intermediate Similarity	NPC251929
0.8219	Intermediate Similarity	NPC260040
0.8194	Intermediate Similarity	NPC310992
0.8194	Intermediate Similarity	NPC87141
0.8158	Intermediate Similarity	NPC469793
0.8158	Intermediate Similarity	NPC19907
0.8158	Intermediate Similarity	NPC469796
0.8148	Intermediate Similarity	NPC33881
0.8133	Intermediate Similarity	NPC309852
0.8108	Intermediate Similarity	NPC54123
0.8108	Intermediate Similarity	NPC304983
0.8108	Intermediate Similarity	NPC225467
0.8082	Intermediate Similarity	NPC286814
0.8082	Intermediate Similarity	NPC256846
0.8082	Intermediate Similarity	NPC139397
0.8028	Intermediate Similarity	NPC268039
0.8028	Intermediate Similarity	NPC251118
0.8026	Intermediate Similarity	NPC293803
0.8	Intermediate Similarity	NPC470045
0.8	Intermediate Similarity	NPC470044
0.8	Intermediate Similarity	NPC251705
0.8	Intermediate Similarity	NPC144947
0.7976	Intermediate Similarity	NPC184663
0.7976	Intermediate Similarity	NPC469546
0.7973	Intermediate Similarity	NPC35734
0.7973	Intermediate Similarity	NPC307176
0.7973	Intermediate Similarity	NPC282593
0.7973	Intermediate Similarity	NPC159577
0.7949	Intermediate Similarity	NPC228911
0.7945	Intermediate Similarity	NPC39157
0.7945	Intermediate Similarity	NPC296697
0.7945	Intermediate Similarity	NPC142754
0.7945	Intermediate Similarity	NPC82477
0.7922	Intermediate Similarity	NPC69408
0.7895	Intermediate Similarity	NPC255021
0.7895	Intermediate Similarity	NPC159497
0.7887	Intermediate Similarity	NPC469662
0.7882	Intermediate Similarity	NPC101651
0.7882	Intermediate Similarity	NPC159748
0.7867	Intermediate Similarity	NPC115023
0.7867	Intermediate Similarity	NPC305501
0.7867	Intermediate Similarity	NPC234707
0.7857	Intermediate Similarity	NPC206060
0.7808	Intermediate Similarity	NPC220210
0.7808	Intermediate Similarity	NPC20181
0.7792	Intermediate Similarity	NPC473171
0.7791	Intermediate Similarity	NPC230064
0.7778	Intermediate Similarity	NPC142683
0.7778	Intermediate Similarity	NPC470813
0.7763	Intermediate Similarity	NPC474488
0.775	Intermediate Similarity	NPC2482
0.7746	Intermediate Similarity	NPC202118
0.7746	Intermediate Similarity	NPC197238
0.7746	Intermediate Similarity	NPC288253
0.7722	Intermediate Similarity	NPC59436
0.7714	Intermediate Similarity	NPC127582
0.7711	Intermediate Similarity	NPC133652
0.7703	Intermediate Similarity	NPC20610
0.7701	Intermediate Similarity	NPC151722
0.7692	Intermediate Similarity	NPC1254
0.7674	Intermediate Similarity	NPC328141
0.7662	Intermediate Similarity	NPC238146
0.7662	Intermediate Similarity	NPC75485
0.7662	Intermediate Similarity	NPC474796
0.7662	Intermediate Similarity	NPC168975
0.7662	Intermediate Similarity	NPC474797
0.7662	Intermediate Similarity	NPC329866
0.7654	Intermediate Similarity	NPC116797
0.7647	Intermediate Similarity	NPC474925
0.7639	Intermediate Similarity	NPC285371
0.7639	Intermediate Similarity	NPC475124
0.7625	Intermediate Similarity	NPC476177
0.7614	Intermediate Similarity	NPC269729
0.7606	Intermediate Similarity	NPC60565
0.76	Intermediate Similarity	NPC182815
0.7595	Intermediate Similarity	NPC472300
0.7571	Intermediate Similarity	NPC472304
0.7571	Intermediate Similarity	NPC276764
0.7564	Intermediate Similarity	NPC65650
0.7564	Intermediate Similarity	NPC255650
0.7558	Intermediate Similarity	NPC477973
0.7531	Intermediate Similarity	NPC287063
0.7531	Intermediate Similarity	NPC472478
0.7529	Intermediate Similarity	NPC93778
0.7528	Intermediate Similarity	NPC274417
0.75	Intermediate Similarity	NPC474537
0.75	Intermediate Similarity	NPC40574
0.75	Intermediate Similarity	NPC469996
0.75	Intermediate Similarity	NPC4827
0.75	Intermediate Similarity	NPC82635
0.75	Intermediate Similarity	NPC189485
0.7471	Intermediate Similarity	NPC191684
0.747	Intermediate Similarity	NPC41539
0.747	Intermediate Similarity	NPC53733
0.7468	Intermediate Similarity	NPC899
0.7444	Intermediate Similarity	NPC5532
0.7444	Intermediate Similarity	NPC61369
0.7444	Intermediate Similarity	NPC469545
0.7439	Intermediate Similarity	NPC121984
0.7439	Intermediate Similarity	NPC475863
0.7439	Intermediate Similarity	NPC278459
0.7439	Intermediate Similarity	NPC90055
0.7439	Intermediate Similarity	NPC471898
0.7439	Intermediate Similarity	NPC474085
0.7439	Intermediate Similarity	NPC470034
0.7439	Intermediate Similarity	NPC3915
0.7439	Intermediate Similarity	NPC99308
0.7436	Intermediate Similarity	NPC166797
0.7436	Intermediate Similarity	NPC20025
0.7432	Intermediate Similarity	NPC323005
0.7429	Intermediate Similarity	NPC56905
0.7429	Intermediate Similarity	NPC27610
0.7412	Intermediate Similarity	NPC95594
0.7412	Intermediate Similarity	NPC477579
0.7412	Intermediate Similarity	NPC235341
0.7407	Intermediate Similarity	NPC27817
0.7407	Intermediate Similarity	NPC283789
0.7407	Intermediate Similarity	NPC472490
0.7403	Intermediate Similarity	NPC470078
0.7403	Intermediate Similarity	NPC181204
0.7403	Intermediate Similarity	NPC223187
0.7403	Intermediate Similarity	NPC5701
0.7397	Intermediate Similarity	NPC212210
0.7381	Intermediate Similarity	NPC473246
0.7381	Intermediate Similarity	NPC85774
0.7381	Intermediate Similarity	NPC470812
0.7381	Intermediate Similarity	NPC476412
0.7381	Intermediate Similarity	NPC214043
0.7375	Intermediate Similarity	NPC107039
0.7375	Intermediate Similarity	NPC471897
0.7375	Intermediate Similarity	NPC471899
0.7353	Intermediate Similarity	NPC100809
0.7353	Intermediate Similarity	NPC250539
0.7353	Intermediate Similarity	NPC209431
0.7349	Intermediate Similarity	NPC3511
0.7349	Intermediate Similarity	NPC472867
0.7349	Intermediate Similarity	NPC472239
0.7349	Intermediate Similarity	NPC142253
0.7349	Intermediate Similarity	NPC310989
0.7349	Intermediate Similarity	NPC163236
0.7349	Intermediate Similarity	NPC103486
0.7342	Intermediate Similarity	NPC476346
0.7333	Intermediate Similarity	NPC176107
0.7333	Intermediate Similarity	NPC475523
0.7326	Intermediate Similarity	NPC470523
0.7317	Intermediate Similarity	NPC476809
0.7317	Intermediate Similarity	NPC267517
0.7317	Intermediate Similarity	NPC108955
0.7317	Intermediate Similarity	NPC104545
0.7317	Intermediate Similarity	NPC474956
0.7308	Intermediate Similarity	NPC109576
0.7308	Intermediate Similarity	NPC180015
0.7308	Intermediate Similarity	NPC56747
0.7308	Intermediate Similarity	NPC130016
0.7303	Intermediate Similarity	NPC250575
0.7297	Intermediate Similarity	NPC470329
0.7294	Intermediate Similarity	NPC70685
0.7294	Intermediate Similarity	NPC476426
0.7294	Intermediate Similarity	NPC472940
0.7294	Intermediate Similarity	NPC469948
0.7294	Intermediate Similarity	NPC472931
0.7284	Intermediate Similarity	NPC260385
0.7284	Intermediate Similarity	NPC280654
0.7284	Intermediate Similarity	NPC110094
0.7284	Intermediate Similarity	NPC80088
0.7284	Intermediate Similarity	NPC253561
0.7284	Intermediate Similarity	NPC470052
0.7273	Intermediate Similarity	NPC477856
0.7273	Intermediate Similarity	NPC85173
0.7273	Intermediate Similarity	NPC214770
0.7262	Intermediate Similarity	NPC470165
0.725	Intermediate Similarity	NPC89294
0.725	Intermediate Similarity	NPC474463
0.725	Intermediate Similarity	NPC470525
0.7241	Intermediate Similarity	NPC474474
0.7241	Intermediate Similarity	NPC470524
0.7241	Intermediate Similarity	NPC472802
0.7241	Intermediate Similarity	NPC224145

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 NPC219232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2279
0.2-0.3	4383
0.3-0.4	1651
0.4-0.5	323
0.5-0.6	204
0.6-0.7	80
0.7-0.8	18
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8219	Intermediate Similarity	NPD4691	Approved
0.8082	Intermediate Similarity	NPD4137	Phase 3
0.7973	Intermediate Similarity	NPD4747	Approved
0.7895	Intermediate Similarity	NPD5733	Approved
0.7895	Intermediate Similarity	NPD4058	Approved
0.7662	Intermediate Similarity	NPD4687	Approved
0.7654	Intermediate Similarity	NPD8028	Phase 2
0.7632	Intermediate Similarity	NPD5276	Approved
0.7467	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7521	Approved
0.7209	Intermediate Similarity	NPD7146	Approved
0.7209	Intermediate Similarity	NPD7334	Approved
0.7209	Intermediate Similarity	NPD6684	Approved
0.7209	Intermediate Similarity	NPD6409	Approved
0.7209	Intermediate Similarity	NPD5330	Approved
0.7176	Intermediate Similarity	NPD3133	Approved
0.7176	Intermediate Similarity	NPD3666	Approved
0.7176	Intermediate Similarity	NPD3665	Phase 1
0.7108	Intermediate Similarity	NPD4695	Discontinued
0.7059	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6903	Approved
0.7045	Intermediate Similarity	NPD6672	Approved
0.7045	Intermediate Similarity	NPD5737	Approved
0.7033	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7900	Approved
0.7011	Intermediate Similarity	NPD3618	Phase 1
0.7	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD7515	Phase 2
0.6977	Remote Similarity	NPD4786	Approved
0.6966	Remote Similarity	NPD5328	Approved
0.6944	Remote Similarity	NPD287	Approved
0.6941	Remote Similarity	NPD4223	Phase 3
0.6941	Remote Similarity	NPD3667	Approved
0.6941	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4221	Approved
0.6932	Remote Similarity	NPD3573	Approved
0.6897	Remote Similarity	NPD5329	Approved
0.6882	Remote Similarity	NPD4697	Phase 3
0.6848	Remote Similarity	NPD7748	Approved
0.6818	Remote Similarity	NPD5690	Phase 2
0.6818	Remote Similarity	NPD5279	Phase 3
0.6809	Remote Similarity	NPD7902	Approved
0.6782	Remote Similarity	NPD4197	Approved
0.6782	Remote Similarity	NPD3668	Phase 3
0.6778	Remote Similarity	NPD4753	Phase 2
0.6778	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7732	Phase 3
0.6667	Remote Similarity	NPD3617	Approved
0.6629	Remote Similarity	NPD4690	Approved
0.6629	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD5205	Approved
0.6629	Remote Similarity	NPD4689	Approved
0.6629	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4693	Phase 3
0.6629	Remote Similarity	NPD5280	Approved
0.6629	Remote Similarity	NPD4623	Approved
0.6629	Remote Similarity	NPD4138	Approved
0.6629	Remote Similarity	NPD4694	Approved
0.6629	Remote Similarity	NPD4688	Approved
0.6596	Remote Similarity	NPD4629	Approved
0.6596	Remote Similarity	NPD5210	Approved
0.6593	Remote Similarity	NPD6673	Approved
0.6593	Remote Similarity	NPD6080	Approved
0.6593	Remote Similarity	NPD6904	Approved
0.6559	Remote Similarity	NPD6399	Phase 3
0.6559	Remote Similarity	NPD4202	Approved
0.6526	Remote Similarity	NPD7614	Phase 1
0.6526	Remote Similarity	NPD5221	Approved
0.6526	Remote Similarity	NPD5222	Approved
0.6526	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5208	Approved
0.6477	Remote Similarity	NPD4788	Approved
0.6458	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD6083	Phase 2
0.6458	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD6050	Approved
0.6444	Remote Similarity	NPD6098	Approved
0.6421	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5695	Phase 3
0.6395	Remote Similarity	NPD4195	Approved
0.6344	Remote Similarity	NPD5207	Approved
0.6344	Remote Similarity	NPD5692	Phase 3
0.6327	Remote Similarity	NPD4696	Approved
0.6327	Remote Similarity	NPD5285	Approved
0.6327	Remote Similarity	NPD5286	Approved
0.6322	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD5284	Approved
0.6277	Remote Similarity	NPD5281	Approved
0.6277	Remote Similarity	NPD5693	Phase 1
0.6277	Remote Similarity	NPD5694	Approved
0.6263	Remote Similarity	NPD5223	Approved
0.6224	Remote Similarity	NPD5696	Approved
0.6207	Remote Similarity	NPD7645	Phase 2
0.62	Remote Similarity	NPD5225	Approved
0.62	Remote Similarity	NPD5226	Approved
0.62	Remote Similarity	NPD5224	Approved
0.62	Remote Similarity	NPD4633	Approved
0.62	Remote Similarity	NPD5211	Phase 2
0.617	Remote Similarity	NPD4096	Approved
0.6162	Remote Similarity	NPD4700	Approved
0.6162	Remote Similarity	NPD6404	Discontinued
0.6154	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6001	Approved
0.6139	Remote Similarity	NPD5174	Approved
0.6139	Remote Similarity	NPD5175	Approved
0.6125	Remote Similarity	NPD7331	Phase 2
0.6122	Remote Similarity	NPD3495	Discontinued
0.6118	Remote Similarity	NPD8039	Approved
0.6118	Remote Similarity	NPD6942	Approved
0.6118	Remote Similarity	NPD7339	Approved
0.6117	Remote Similarity	NPD6412	Phase 2
0.6078	Remote Similarity	NPD5141	Approved
0.6078	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4139	Approved
0.6067	Remote Similarity	NPD4692	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6047	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5133	Approved
0.6042	Remote Similarity	NPD7631	Approved
0.6038	Remote Similarity	NPD6650	Approved
0.6038	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6373	Approved
0.598	Remote Similarity	NPD4754	Approved
0.5962	Remote Similarity	NPD5697	Approved
0.5957	Remote Similarity	NPD4518	Approved
0.5952	Remote Similarity	NPD4243	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5938	Remote Similarity	NPD8034	Phase 2
0.5938	Remote Similarity	NPD8035	Phase 2
0.5938	Remote Similarity	NPD7609	Phase 3
0.5938	Remote Similarity	NPD6411	Approved
0.5918	Remote Similarity	NPD5654	Approved
0.5905	Remote Similarity	NPD6011	Approved
0.5905	Remote Similarity	NPD4729	Approved
0.5905	Remote Similarity	NPD5168	Approved
0.5905	Remote Similarity	NPD5128	Approved
0.5905	Remote Similarity	NPD4730	Approved
0.5905	Remote Similarity	NPD7320	Approved
0.59	Remote Similarity	NPD7638	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.5882	Remote Similarity	NPD5091	Approved
0.5875	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4767	Approved
0.5865	Remote Similarity	NPD4768	Approved
0.5865	Remote Similarity	NPD6008	Approved
0.5849	Remote Similarity	NPD6014	Approved
0.5849	Remote Similarity	NPD6013	Approved
0.5849	Remote Similarity	NPD6012	Approved
0.5842	Remote Similarity	NPD7640	Approved
0.5842	Remote Similarity	NPD7639	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD6052	Approved
0.5823	Remote Similarity	NPD4193	Approved
0.5823	Remote Similarity	NPD4191	Approved
0.5823	Remote Similarity	NPD4192	Approved
0.5823	Remote Similarity	NPD4194	Approved
0.5814	Remote Similarity	NPD4785	Approved
0.5814	Remote Similarity	NPD4784	Approved
0.581	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD6614	Approved
0.5802	Remote Similarity	NPD7341	Phase 2
0.58	Remote Similarity	NPD5959	Approved
0.5794	Remote Similarity	NPD5247	Approved
0.5794	Remote Similarity	NPD5135	Approved
0.5794	Remote Similarity	NPD5248	Approved
0.5794	Remote Similarity	NPD5250	Approved
0.5794	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5251	Approved
0.5794	Remote Similarity	NPD5169	Approved
0.5794	Remote Similarity	NPD4634	Approved
0.5794	Remote Similarity	NPD5249	Phase 3
0.578	Remote Similarity	NPD6858	Approved
0.578	Remote Similarity	NPD7094	Approved
0.5778	Remote Similarity	NPD7525	Registered
0.5766	Remote Similarity	NPD7115	Discovery
0.5755	Remote Similarity	NPD6686	Approved
0.5747	Remote Similarity	NPD8264	Approved
0.5741	Remote Similarity	NPD5127	Approved
0.5741	Remote Similarity	NPD5217	Approved
0.5741	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5215	Approved
0.5741	Remote Similarity	NPD5216	Approved
0.5732	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6051	Approved
0.5729	Remote Similarity	NPD5764	Clinical (unspecified phase)

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