NPASS Compound

Structure

NPC33881 OpenBabel07101718222D 31 35 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 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 3.4641 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 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 -1.7321 2.0000 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 0.0000 -1.0000 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 -0.0000 2.0000 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 2.5981 -2.5000 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 -2.5981 0.5000 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 3.4641 -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 3.4641 -3.0000 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 0.0000 0.0000 0.0000 C 0 0 2 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 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 1 17 2 0 0 0 0 2 18 1 0 0 0 0 4 26 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 7 22 2 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 29 2 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 6 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 25 3 1 1 0 0 0 26 27 1 1 0 0 0 27 5 1 6 0 0 0 28 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.25
Volume:	457.977
LogP:	4.782
LogD:	3.073
LogS:	-4.111
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.259
Fsp3:	0.536
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.966
MDCK Permeability:	1.69503218785394e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	84.66059112548828%
Volume Distribution (VD):	1.619
Pgp-substrate:	7.400080680847168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.38
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.368
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.569
CYP3A4-substrate:	0.885

ADMET: Excretion

Clearance (CL):	5.809
Half-life (T1/2):	0.552

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.207
Rat Oral Acute Toxicity:	0.478
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.919
Carcinogencity:	0.878
Eye Corrosion:	0.005
Eye Irritation:	0.374
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC33881

Natural Product ID:	NPC33881
*Common Name:**	28-Nor-Isoiguesterin-17-Carbaldehyde
IUPAC Name:	(4aS,6aR,6aS,14aS,14bS)-10-hydroxy-6a,6a,9,14a-tetramethyl-2-methylidene-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-4a-carbaldehyde
Synonyms:
Standard InCHIKey:	KGQOHECLTONQOT-HKFGFSCZSA-N
Standard InCHI:	InChI=1S/C28H34O3/c1-17-8-9-28(16-29)13-12-26(4)22-7-6-19-18(2)24(31)21(30)15-20(19)25(22,3)10-11-27(26,5)23(28)14-17/h6-7,15-16,23,31H,1,8-14H2,2-5H3/t23-,25-,26+,27-,28+/m0/s1
SMILES:	O=C[C@@]12CCC(=C)C[C@H]2[C@]2([C@@](CC1)(C)C1=CC=C3C(=CC(=O)C(=C3C)O)[C@@]1(CC2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478171
PubChem CID:	10645721
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones

*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
NPO26085	Salacia kraussii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644053]
NPO26085	Salacia kraussii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.094	ug.mL-1	PMID[468926]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0799	ug.mL-1	PMID[468926]

☑ 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 NPC33881 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	185
0.1-0.2	1414
0.2-0.3	6804
0.3-0.4	16599
0.4-0.5	9162
0.5-0.6	6122
0.6-0.7	2015
0.7-0.8	370
0.8-0.85	17
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9367	High Similarity	NPC287063
0.925	High Similarity	NPC475863
0.9012	High Similarity	NPC470034
0.8861	High Similarity	NPC112680
0.8625	High Similarity	NPC292589
0.8571	High Similarity	NPC53733
0.8539	High Similarity	NPC211230
0.8539	High Similarity	NPC263780
0.8537	High Similarity	NPC27817
0.8471	Intermediate Similarity	NPC53385
0.8444	Intermediate Similarity	NPC474882
0.8427	Intermediate Similarity	NPC174167
0.8427	Intermediate Similarity	NPC470036
0.8409	Intermediate Similarity	NPC65615
0.8409	Intermediate Similarity	NPC68148
0.8409	Intermediate Similarity	NPC112454
0.8395	Intermediate Similarity	NPC1254
0.8353	Intermediate Similarity	NPC309309
0.8353	Intermediate Similarity	NPC291999
0.8242	Intermediate Similarity	NPC474328
0.8242	Intermediate Similarity	NPC23170
0.8193	Intermediate Similarity	NPC115515
0.8171	Intermediate Similarity	NPC110725
0.8152	Intermediate Similarity	NPC777
0.8148	Intermediate Similarity	NPC128346
0.8148	Intermediate Similarity	NPC219232
0.8148	Intermediate Similarity	NPC211641
0.8125	Intermediate Similarity	NPC190035
0.8118	Intermediate Similarity	NPC225515
0.8118	Intermediate Similarity	NPC99308
0.8118	Intermediate Similarity	NPC121984
0.8095	Intermediate Similarity	NPC170793
0.8023	Intermediate Similarity	NPC310989
0.8	Intermediate Similarity	NPC18955
0.8	Intermediate Similarity	NPC108955
0.8	Intermediate Similarity	NPC474509
0.8	Intermediate Similarity	NPC2482
0.7976	Intermediate Similarity	NPC189485
0.7955	Intermediate Similarity	NPC469993
0.7931	Intermediate Similarity	NPC307258
0.7912	Intermediate Similarity	NPC252737
0.7907	Intermediate Similarity	NPC3915
0.7907	Intermediate Similarity	NPC55869
0.7889	Intermediate Similarity	NPC206060
0.7889	Intermediate Similarity	NPC474474
0.7875	Intermediate Similarity	NPC286814
0.7848	Intermediate Similarity	NPC193770
0.7841	Intermediate Similarity	NPC180834
0.7816	Intermediate Similarity	NPC103486
0.7802	Intermediate Similarity	NPC184663
0.7766	Intermediate Similarity	NPC147232
0.7753	Intermediate Similarity	NPC133652
0.7753	Intermediate Similarity	NPC241512
0.7753	Intermediate Similarity	NPC6185
0.7753	Intermediate Similarity	NPC255174
0.7753	Intermediate Similarity	NPC8518
0.7753	Intermediate Similarity	NPC263997
0.7753	Intermediate Similarity	NPC474537
0.7753	Intermediate Similarity	NPC132228
0.7753	Intermediate Similarity	NPC32037
0.775	Intermediate Similarity	NPC142754
0.775	Intermediate Similarity	NPC82477
0.775	Intermediate Similarity	NPC296697
0.775	Intermediate Similarity	NPC310992
0.775	Intermediate Similarity	NPC155198
0.775	Intermediate Similarity	NPC39157
0.7742	Intermediate Similarity	NPC250575
0.7738	Intermediate Similarity	NPC469793
0.7738	Intermediate Similarity	NPC92080
0.7738	Intermediate Similarity	NPC469796
0.7727	Intermediate Similarity	NPC70834
0.7701	Intermediate Similarity	NPC4166
0.7701	Intermediate Similarity	NPC471898
0.7692	Intermediate Similarity	NPC230387
0.7683	Intermediate Similarity	NPC225467
0.7677	Intermediate Similarity	NPC213366
0.7674	Intermediate Similarity	NPC90965
0.7667	Intermediate Similarity	NPC95594
0.7667	Intermediate Similarity	NPC477579
0.7667	Intermediate Similarity	NPC235341
0.7667	Intermediate Similarity	NPC94666
0.7654	Intermediate Similarity	NPC474060
0.764	Intermediate Similarity	NPC96095
0.764	Intermediate Similarity	NPC237712
0.7634	Intermediate Similarity	NPC301244
0.7634	Intermediate Similarity	NPC230064
0.7625	Intermediate Similarity	NPC20181
0.7625	Intermediate Similarity	NPC220210
0.7619	Intermediate Similarity	NPC473171
0.7614	Intermediate Similarity	NPC69101
0.7614	Intermediate Similarity	NPC251779
0.7614	Intermediate Similarity	NPC311092
0.7609	Intermediate Similarity	NPC477973
0.7604	Intermediate Similarity	NPC21728
0.759	Intermediate Similarity	NPC474488
0.7582	Intermediate Similarity	NPC73064
0.7582	Intermediate Similarity	NPC470523
0.7582	Intermediate Similarity	NPC71507
0.7582	Intermediate Similarity	NPC93778
0.7558	Intermediate Similarity	NPC82635
0.7558	Intermediate Similarity	NPC30321
0.7556	Intermediate Similarity	NPC274724
0.7556	Intermediate Similarity	NPC474680
0.7556	Intermediate Similarity	NPC133954
0.7556	Intermediate Similarity	NPC469948
0.7531	Intermediate Similarity	NPC188292
0.7531	Intermediate Similarity	NPC260474
0.7528	Intermediate Similarity	NPC105803
0.7528	Intermediate Similarity	NPC41539
0.7527	Intermediate Similarity	NPC46441
0.7527	Intermediate Similarity	NPC129913
0.75	Intermediate Similarity	NPC142244
0.75	Intermediate Similarity	NPC274050
0.75	Intermediate Similarity	NPC474925
0.75	Intermediate Similarity	NPC1753
0.75	Intermediate Similarity	NPC474085
0.75	Intermediate Similarity	NPC472802
0.75	Intermediate Similarity	NPC470524
0.75	Intermediate Similarity	NPC116797
0.75	Intermediate Similarity	NPC474511
0.75	Intermediate Similarity	NPC263272
0.75	Intermediate Similarity	NPC162632
0.75	Intermediate Similarity	NPC267691
0.7474	Intermediate Similarity	NPC160413
0.7474	Intermediate Similarity	NPC80365
0.7473	Intermediate Similarity	NPC118648
0.7473	Intermediate Similarity	NPC213412
0.7473	Intermediate Similarity	NPC31564
0.7473	Intermediate Similarity	NPC51014
0.7473	Intermediate Similarity	NPC158393
0.7473	Intermediate Similarity	NPC74363
0.7473	Intermediate Similarity	NPC327115
0.7473	Intermediate Similarity	NPC474778
0.7473	Intermediate Similarity	NPC474732
0.7473	Intermediate Similarity	NPC474733
0.7473	Intermediate Similarity	NPC475022
0.7473	Intermediate Similarity	NPC145879
0.7473	Intermediate Similarity	NPC222613
0.7473	Intermediate Similarity	NPC475862
0.7471	Intermediate Similarity	NPC474113
0.747	Intermediate Similarity	NPC474562
0.7447	Intermediate Similarity	NPC4036
0.7447	Intermediate Similarity	NPC145067
0.7447	Intermediate Similarity	NPC65120
0.7447	Intermediate Similarity	NPC474525
0.7447	Intermediate Similarity	NPC233455
0.7447	Intermediate Similarity	NPC158030
0.7447	Intermediate Similarity	NPC99380
0.7444	Intermediate Similarity	NPC85774
0.7444	Intermediate Similarity	NPC473246
0.7444	Intermediate Similarity	NPC214043
0.7444	Intermediate Similarity	NPC87552
0.7439	Intermediate Similarity	NPC139397
0.7419	Intermediate Similarity	NPC474686
0.7419	Intermediate Similarity	NPC95246
0.7419	Intermediate Similarity	NPC474972
0.7419	Intermediate Similarity	NPC161751
0.7419	Intermediate Similarity	NPC474700
0.7416	Intermediate Similarity	NPC48362
0.7412	Intermediate Similarity	NPC293803
0.7407	Intermediate Similarity	NPC290350
0.7407	Intermediate Similarity	NPC4370
0.74	Intermediate Similarity	NPC179208
0.7396	Intermediate Similarity	NPC280725
0.7391	Intermediate Similarity	NPC58063
0.7391	Intermediate Similarity	NPC158141
0.7391	Intermediate Similarity	NPC475740
0.7391	Intermediate Similarity	NPC173089
0.7391	Intermediate Similarity	NPC136548
0.7386	Intermediate Similarity	NPC472478
0.7386	Intermediate Similarity	NPC74086
0.7381	Intermediate Similarity	NPC474228
0.7381	Intermediate Similarity	NPC303613
0.7375	Intermediate Similarity	NPC268039
0.7368	Intermediate Similarity	NPC12722
0.7368	Intermediate Similarity	NPC214756
0.7368	Intermediate Similarity	NPC295643
0.7368	Intermediate Similarity	NPC272075
0.7363	Intermediate Similarity	NPC472940
0.7363	Intermediate Similarity	NPC472931
0.7356	Intermediate Similarity	NPC476808
0.7349	Intermediate Similarity	NPC260040
0.7349	Intermediate Similarity	NPC159577
0.7349	Intermediate Similarity	NPC282593
0.7349	Intermediate Similarity	NPC307176
0.7349	Intermediate Similarity	NPC251929
0.7349	Intermediate Similarity	NPC35734
0.7349	Intermediate Similarity	NPC2634
0.7349	Intermediate Similarity	NPC265782
0.7347	Intermediate Similarity	NPC471966
0.734	Intermediate Similarity	NPC474209
0.734	Intermediate Similarity	NPC191684
0.734	Intermediate Similarity	NPC475823
0.734	Intermediate Similarity	NPC85173
0.7326	Intermediate Similarity	NPC26504
0.7326	Intermediate Similarity	NPC470525
0.7326	Intermediate Similarity	NPC19907
0.732	Intermediate Similarity	NPC157113
0.732	Intermediate Similarity	NPC9487
0.732	Intermediate Similarity	NPC473158

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 NPC33881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1630
0.2-0.3	4303
0.3-0.4	2243
0.4-0.5	463
0.5-0.6	203
0.6-0.7	113
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4695	Discontinued
0.7711	Intermediate Similarity	NPD5733	Approved
0.7667	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD4687	Approved
0.75	Intermediate Similarity	NPD4058	Approved
0.7473	Intermediate Similarity	NPD5280	Approved
0.7473	Intermediate Similarity	NPD4694	Approved
0.747	Intermediate Similarity	NPD5276	Approved
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7439	Intermediate Similarity	NPD4137	Phase 3
0.7386	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5329	Approved
0.7356	Intermediate Similarity	NPD3617	Approved
0.7349	Intermediate Similarity	NPD4747	Approved
0.7349	Intermediate Similarity	NPD4691	Approved
0.7303	Intermediate Similarity	NPD8028	Phase 2
0.7292	Intermediate Similarity	NPD7748	Approved
0.7253	Intermediate Similarity	NPD4786	Approved
0.7253	Intermediate Similarity	NPD4197	Approved
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7234	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7097	Intermediate Similarity	NPD5690	Phase 2
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7071	Intermediate Similarity	NPD7902	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7033	Intermediate Similarity	NPD4223	Phase 3
0.7033	Intermediate Similarity	NPD4221	Approved
0.6947	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5737	Approved
0.6947	Remote Similarity	NPD6672	Approved
0.6907	Remote Similarity	NPD6079	Approved
0.6905	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6083	Phase 2
0.69	Remote Similarity	NPD6084	Phase 2
0.6869	Remote Similarity	NPD5695	Phase 3
0.6869	Remote Similarity	NPD4629	Approved
0.6869	Remote Similarity	NPD5210	Approved
0.6837	Remote Similarity	NPD5133	Approved
0.68	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5222	Approved
0.68	Remote Similarity	NPD7614	Phase 1
0.68	Remote Similarity	NPD5221	Approved
0.6774	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4788	Approved
0.6768	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7900	Approved
0.6737	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD7521	Approved
0.6737	Remote Similarity	NPD4693	Phase 3
0.6737	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6737	Remote Similarity	NPD4689	Approved
0.6737	Remote Similarity	NPD7334	Approved
0.6737	Remote Similarity	NPD6409	Approved
0.6737	Remote Similarity	NPD5205	Approved
0.6737	Remote Similarity	NPD4138	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD7146	Approved
0.6737	Remote Similarity	NPD4690	Approved
0.6737	Remote Similarity	NPD4688	Approved
0.6735	Remote Similarity	NPD5284	Approved
0.6735	Remote Similarity	NPD6050	Approved
0.6735	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5173	Approved
0.6733	Remote Similarity	NPD4755	Approved
0.6702	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD4096	Approved
0.6633	Remote Similarity	NPD5692	Phase 3
0.6602	Remote Similarity	NPD5286	Approved
0.6602	Remote Similarity	NPD5285	Approved
0.6602	Remote Similarity	NPD4700	Approved
0.6602	Remote Similarity	NPD4696	Approved
0.6598	Remote Similarity	NPD6903	Approved
0.6598	Remote Similarity	NPD4518	Approved
0.6566	Remote Similarity	NPD5694	Approved
0.6562	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5223	Approved
0.6531	Remote Similarity	NPD6904	Approved
0.6531	Remote Similarity	NPD6673	Approved
0.6531	Remote Similarity	NPD6080	Approved
0.6522	Remote Similarity	NPD7645	Phase 2
0.6476	Remote Similarity	NPD5225	Approved
0.6476	Remote Similarity	NPD5211	Phase 2
0.6476	Remote Similarity	NPD4633	Approved
0.6476	Remote Similarity	NPD5224	Approved
0.6476	Remote Similarity	NPD5226	Approved
0.6471	Remote Similarity	NPD7732	Phase 3
0.6458	Remote Similarity	NPD1696	Phase 3
0.6449	Remote Similarity	NPD6402	Approved
0.6449	Remote Similarity	NPD7128	Approved
0.6449	Remote Similarity	NPD5739	Approved
0.6449	Remote Similarity	NPD6675	Approved
0.642	Remote Similarity	NPD287	Approved
0.6415	Remote Similarity	NPD5175	Approved
0.6415	Remote Similarity	NPD4754	Approved
0.6415	Remote Similarity	NPD5174	Approved
0.64	Remote Similarity	NPD6411	Approved
0.6392	Remote Similarity	NPD6098	Approved
0.6355	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5141	Approved
0.6344	Remote Similarity	NPD4195	Approved
0.633	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD6881	Approved
0.633	Remote Similarity	NPD6899	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.63	Remote Similarity	NPD5207	Approved
0.6296	Remote Similarity	NPD4768	Approved
0.6296	Remote Similarity	NPD4767	Approved
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7331	Phase 2
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD6372	Approved
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD8264	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD6922	Approved
0.6239	Remote Similarity	NPD6412	Phase 2
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD5693	Phase 1
0.6216	Remote Similarity	NPD7290	Approved
0.6216	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD7102	Approved
0.6214	Remote Similarity	NPD5654	Approved
0.6211	Remote Similarity	NPD4139	Approved
0.6211	Remote Similarity	NPD4692	Approved
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD4729	Approved
0.6182	Remote Similarity	NPD5128	Approved
0.6182	Remote Similarity	NPD5168	Approved
0.6182	Remote Similarity	NPD4730	Approved
0.618	Remote Similarity	NPD7144	Approved
0.618	Remote Similarity	NPD7143	Approved
0.618	Remote Similarity	NPD4789	Approved
0.6168	Remote Similarity	NPD5091	Approved
0.6161	Remote Similarity	NPD6617	Approved
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8130	Phase 1
0.6161	Remote Similarity	NPD6649	Approved
0.6161	Remote Similarity	NPD6869	Approved
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD6924	Approved
0.6154	Remote Similarity	NPD6926	Approved
0.6132	Remote Similarity	NPD6404	Discontinued
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6118	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7151	Approved
0.6111	Remote Similarity	NPD7152	Approved
0.6111	Remote Similarity	NPD7150	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD6882	Approved
0.61	Remote Similarity	NPD5208	Approved
0.6095	Remote Similarity	NPD5959	Approved
0.6071	Remote Similarity	NPD5169	Approved
0.6071	Remote Similarity	NPD5250	Approved
0.6071	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5251	Approved
0.6071	Remote Similarity	NPD5249	Phase 3
0.6071	Remote Similarity	NPD4634	Approved
0.6071	Remote Similarity	NPD5248	Approved
0.6071	Remote Similarity	NPD5247	Approved
0.6071	Remote Similarity	NPD5135	Approved
0.6058	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7638	Approved
0.6022	Remote Similarity	NPD6933	Approved
0.6018	Remote Similarity	NPD5215	Approved
0.6018	Remote Similarity	NPD5127	Approved
0.6018	Remote Similarity	NPD5216	Approved
0.6018	Remote Similarity	NPD5217	Approved
0.6	Remote Similarity	NPD8328	Phase 3
0.5981	Remote Similarity	NPD7639	Approved
0.5981	Remote Similarity	NPD7640	Approved
0.5979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4784	Approved
0.5978	Remote Similarity	NPD4785	Approved
0.5977	Remote Similarity	NPD7341	Phase 2
0.5962	Remote Similarity	NPD5282	Discontinued
0.5957	Remote Similarity	NPD6925	Approved
0.5957	Remote Similarity	NPD6932	Approved
0.5957	Remote Similarity	NPD5776	Phase 2
0.5957	Remote Similarity	NPD4756	Discovery
0.5948	Remote Similarity	NPD6868	Approved
0.5943	Remote Similarity	NPD3495	Discontinued
0.5938	Remote Similarity	NPD7525	Registered
0.5934	Remote Similarity	NPD4243	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