NPASS Compound

Structure

NPC291999 OpenBabel07101719152D 31 35 0 0 1 0 0 0 0 0999 V2000 -3.4641 -4.0000 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 -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 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 -3.0000 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 1.5000 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 1.7321 -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 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 0.8660 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 1.7321 3.0000 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 1.7321 2.0000 0.0000 C 0 0 2 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 -2.5981 -1.5000 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 -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 2 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 -0.0000 0.0000 C 0 0 1 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 -0.0000 -1.0000 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 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 1 0 0 0 0 4 27 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 18 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 18 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 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 16 1 6 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 6 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.28
Volume:	463.25
LogP:	5.41
LogD:	3.915
LogS:	-4.464
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	5.004
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	1.2598557077581063e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.208
30% Bioavailability (F30%):	0.309

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.486
Plasma Protein Binding (PPB):	99.94330596923828%
Volume Distribution (VD):	2.873
Pgp-substrate:	3.0146992206573486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.208
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.576
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.865

ADMET: Excretion

Clearance (CL):	3.642
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.297
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.336
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.855
Skin Sensitization:	0.922
Carcinogencity:	0.108
Eye Corrosion:	0.004
Eye Irritation:	0.329
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC291999

Natural Product ID:	NPC291999
*Common Name:**	Isoiguesterol
IUPAC Name:	(6aS,6bS,8aR,11R,12aR,14aR)-3-hydroxy-11-(hydroxymethyl)-4,6a,6b,8a,14a-pentamethyl-8,9,10,11,12,12a,13,14-octahydro-7H-picen-2-one
Synonyms:	Isoiguesterol
Standard InCHIKey:	RRKSDDREVOXSJD-VOEASNBBSA-N
Standard InCHI:	InChI=1S/C28H38O3/c1-17-19-6-7-22-26(3,20(19)15-21(30)24(17)31)11-13-28(5)23-14-18(16-29)8-9-25(23,2)10-12-27(22,28)4/h6-7,15,18,23,29,31H,8-14,16H2,1-5H3/t18-,23-,25-,26+,27-,28+/m1/s1
SMILES:	CC1=C(C(=O)C=C2C1=CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@H](CC[C@]3(C)CC[C@]12C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480292
PubChem CID:	10477355
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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2.43	ug.mL-1	PMID[447459]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.0229	ug.mL-1	PMID[447459]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0541	ug.mL-1	PMID[447459]

☑ 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 NPC291999 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	181
0.1-0.2	1300
0.2-0.3	5600
0.3-0.4	16791
0.4-0.5	8825
0.5-0.6	6434
0.6-0.7	2960
0.7-0.8	574
0.8-0.85	18
0.85-0.9	11
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC309309
0.9872	High Similarity	NPC53385
0.8953	High Similarity	NPC211230
0.8851	High Similarity	NPC474882
0.8846	High Similarity	NPC112680
0.8636	High Similarity	NPC474328
0.8621	High Similarity	NPC174167
0.8621	High Similarity	NPC470036
0.8608	High Similarity	NPC292589
0.8605	High Similarity	NPC112454
0.8605	High Similarity	NPC65615
0.8605	High Similarity	NPC68148
0.8554	High Similarity	NPC53733
0.8523	High Similarity	NPC263780
0.8427	Intermediate Similarity	NPC23170
0.8415	Intermediate Similarity	NPC287063
0.8395	Intermediate Similarity	NPC72507
0.8353	Intermediate Similarity	NPC33881
0.8333	Intermediate Similarity	NPC777
0.8313	Intermediate Similarity	NPC475863
0.8313	Intermediate Similarity	NPC121984
0.8214	Intermediate Similarity	NPC310989
0.8193	Intermediate Similarity	NPC18955
0.8193	Intermediate Similarity	NPC2482
0.8118	Intermediate Similarity	NPC237795
0.8118	Intermediate Similarity	NPC82538
0.8095	Intermediate Similarity	NPC3915
0.8095	Intermediate Similarity	NPC225515
0.8095	Intermediate Similarity	NPC470034
0.8068	Intermediate Similarity	NPC230387
0.8023	Intermediate Similarity	NPC180834
0.8021	Intermediate Similarity	NPC213366
0.8	Intermediate Similarity	NPC103486
0.7976	Intermediate Similarity	NPC108955
0.7952	Intermediate Similarity	NPC470396
0.7952	Intermediate Similarity	NPC99168
0.7952	Intermediate Similarity	NPC474989
0.7952	Intermediate Similarity	NPC22955
0.7949	Intermediate Similarity	NPC216460
0.7949	Intermediate Similarity	NPC32055
0.7931	Intermediate Similarity	NPC469993
0.7927	Intermediate Similarity	NPC106364
0.7927	Intermediate Similarity	NPC92080
0.7882	Intermediate Similarity	NPC55869
0.7882	Intermediate Similarity	NPC6663
0.7857	Intermediate Similarity	NPC291379
0.7857	Intermediate Similarity	NPC27817
0.7857	Intermediate Similarity	NPC474113
0.7857	Intermediate Similarity	NPC53744
0.7841	Intermediate Similarity	NPC94666
0.7831	Intermediate Similarity	NPC40394
0.7831	Intermediate Similarity	NPC101475
0.7831	Intermediate Similarity	NPC34177
0.7831	Intermediate Similarity	NPC157996
0.7816	Intermediate Similarity	NPC472265
0.7816	Intermediate Similarity	NPC237712
0.7816	Intermediate Similarity	NPC33913
0.7805	Intermediate Similarity	NPC34700
0.7805	Intermediate Similarity	NPC138374
0.7802	Intermediate Similarity	NPC301244
0.7778	Intermediate Similarity	NPC471799
0.7778	Intermediate Similarity	NPC477973
0.7753	Intermediate Similarity	NPC470523
0.7753	Intermediate Similarity	NPC71507
0.7753	Intermediate Similarity	NPC73064
0.7753	Intermediate Similarity	NPC93778
0.7742	Intermediate Similarity	NPC147232
0.7738	Intermediate Similarity	NPC300499
0.7738	Intermediate Similarity	NPC158662
0.7738	Intermediate Similarity	NPC196753
0.7738	Intermediate Similarity	NPC253807
0.7738	Intermediate Similarity	NPC98386
0.7738	Intermediate Similarity	NPC230295
0.7738	Intermediate Similarity	NPC30321
0.7738	Intermediate Similarity	NPC189485
0.7727	Intermediate Similarity	NPC474680
0.7727	Intermediate Similarity	NPC32037
0.7727	Intermediate Similarity	NPC132228
0.7727	Intermediate Similarity	NPC474537
0.7727	Intermediate Similarity	NPC241512
0.7727	Intermediate Similarity	NPC6185
0.7727	Intermediate Similarity	NPC8518
0.7727	Intermediate Similarity	NPC274724
0.7727	Intermediate Similarity	NPC469948
0.7727	Intermediate Similarity	NPC133652
0.7727	Intermediate Similarity	NPC133954
0.7727	Intermediate Similarity	NPC263997
0.7711	Intermediate Similarity	NPC290598
0.7711	Intermediate Similarity	NPC27765
0.7711	Intermediate Similarity	NPC265328
0.7711	Intermediate Similarity	NPC120098
0.7711	Intermediate Similarity	NPC30590
0.7711	Intermediate Similarity	NPC106432
0.7711	Intermediate Similarity	NPC122418
0.7701	Intermediate Similarity	NPC70834
0.7701	Intermediate Similarity	NPC307258
0.7701	Intermediate Similarity	NPC105803
0.7692	Intermediate Similarity	NPC129913
0.7692	Intermediate Similarity	NPC212369
0.7692	Intermediate Similarity	NPC46441
0.7692	Intermediate Similarity	NPC252737
0.7683	Intermediate Similarity	NPC100334
0.7683	Intermediate Similarity	NPC471797
0.7674	Intermediate Similarity	NPC116202
0.7674	Intermediate Similarity	NPC471898
0.7674	Intermediate Similarity	NPC6434
0.7667	Intermediate Similarity	NPC206060
0.7667	Intermediate Similarity	NPC472802
0.7667	Intermediate Similarity	NPC1753
0.7667	Intermediate Similarity	NPC474511
0.7667	Intermediate Similarity	NPC470524
0.7654	Intermediate Similarity	NPC242001
0.764	Intermediate Similarity	NPC474732
0.764	Intermediate Similarity	NPC74363
0.764	Intermediate Similarity	NPC158393
0.764	Intermediate Similarity	NPC474778
0.764	Intermediate Similarity	NPC51014
0.764	Intermediate Similarity	NPC327115
0.764	Intermediate Similarity	NPC213412
0.764	Intermediate Similarity	NPC475862
0.764	Intermediate Similarity	NPC56588
0.764	Intermediate Similarity	NPC474733
0.764	Intermediate Similarity	NPC145879
0.764	Intermediate Similarity	NPC31564
0.7634	Intermediate Similarity	NPC80365
0.7634	Intermediate Similarity	NPC160413
0.7619	Intermediate Similarity	NPC476811
0.7619	Intermediate Similarity	NPC90979
0.7619	Intermediate Similarity	NPC472805
0.7614	Intermediate Similarity	NPC96095
0.7614	Intermediate Similarity	NPC473246
0.7614	Intermediate Similarity	NPC85774
0.7614	Intermediate Similarity	NPC214043
0.7609	Intermediate Similarity	NPC65120
0.7609	Intermediate Similarity	NPC4036
0.7609	Intermediate Similarity	NPC474525
0.7609	Intermediate Similarity	NPC158030
0.7609	Intermediate Similarity	NPC145067
0.7609	Intermediate Similarity	NPC233455
0.7595	Intermediate Similarity	NPC197805
0.759	Intermediate Similarity	NPC471468
0.7586	Intermediate Similarity	NPC48362
0.7586	Intermediate Similarity	NPC69101
0.7586	Intermediate Similarity	NPC20853
0.7586	Intermediate Similarity	NPC251779
0.7582	Intermediate Similarity	NPC474686
0.7582	Intermediate Similarity	NPC95246
0.7582	Intermediate Similarity	NPC184663
0.7582	Intermediate Similarity	NPC210216
0.7582	Intermediate Similarity	NPC474972
0.7582	Intermediate Similarity	NPC161751
0.7564	Intermediate Similarity	NPC163678
0.7558	Intermediate Similarity	NPC295131
0.7556	Intermediate Similarity	NPC475740
0.7556	Intermediate Similarity	NPC136548
0.7556	Intermediate Similarity	NPC173089
0.7556	Intermediate Similarity	NPC475772
0.7556	Intermediate Similarity	NPC158141
0.7556	Intermediate Similarity	NPC220930
0.7556	Intermediate Similarity	NPC272039
0.7556	Intermediate Similarity	NPC58063
0.7553	Intermediate Similarity	NPC280725
0.7531	Intermediate Similarity	NPC145498
0.7529	Intermediate Similarity	NPC18603
0.7529	Intermediate Similarity	NPC476808
0.7529	Intermediate Similarity	NPC307965
0.7529	Intermediate Similarity	NPC76931
0.7528	Intermediate Similarity	NPC191965
0.7527	Intermediate Similarity	NPC250575
0.7527	Intermediate Similarity	NPC242637
0.7527	Intermediate Similarity	NPC295643
0.7527	Intermediate Similarity	NPC214756
0.7527	Intermediate Similarity	NPC12722
0.7527	Intermediate Similarity	NPC272075
0.75	Intermediate Similarity	NPC208999
0.75	Intermediate Similarity	NPC321016
0.75	Intermediate Similarity	NPC474789
0.75	Intermediate Similarity	NPC52108
0.75	Intermediate Similarity	NPC107059
0.75	Intermediate Similarity	NPC250621
0.75	Intermediate Similarity	NPC475823
0.75	Intermediate Similarity	NPC38952
0.75	Intermediate Similarity	NPC85173
0.75	Intermediate Similarity	NPC470525
0.75	Intermediate Similarity	NPC321381
0.75	Intermediate Similarity	NPC110725
0.75	Intermediate Similarity	NPC474209
0.7474	Intermediate Similarity	NPC62516
0.7474	Intermediate Similarity	NPC473158
0.7474	Intermediate Similarity	NPC157113
0.7474	Intermediate Similarity	NPC88847
0.7473	Intermediate Similarity	NPC471722
0.7473	Intermediate Similarity	NPC473242
0.7473	Intermediate Similarity	NPC229612
0.7473	Intermediate Similarity	NPC17733
0.7473	Intermediate Similarity	NPC474474
0.7473	Intermediate Similarity	NPC474512
0.7473	Intermediate Similarity	NPC7280
0.7473	Intermediate Similarity	NPC290690
0.7473	Intermediate Similarity	NPC470629

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 NPC291999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1546
0.2-0.3	4174
0.3-0.4	2345
0.4-0.5	549
0.5-0.6	159
0.6-0.7	184
0.7-0.8	22
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD7285	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD5279	Phase 3
0.7765	Intermediate Similarity	NPD4695	Discontinued
0.7647	Intermediate Similarity	NPD7645	Phase 2
0.7609	Intermediate Similarity	NPD7515	Phase 2
0.7529	Intermediate Similarity	NPD3617	Approved
0.7444	Intermediate Similarity	NPD5280	Approved
0.7444	Intermediate Similarity	NPD4694	Approved
0.7416	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3665	Phase 1
0.7416	Intermediate Similarity	NPD3666	Approved
0.7416	Intermediate Similarity	NPD4786	Approved
0.7391	Intermediate Similarity	NPD4753	Phase 2
0.7386	Intermediate Similarity	NPD3667	Approved
0.7381	Intermediate Similarity	NPD7339	Approved
0.7381	Intermediate Similarity	NPD6942	Approved
0.7333	Intermediate Similarity	NPD5329	Approved
0.7294	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7748	Approved
0.7262	Intermediate Similarity	NPD6924	Approved
0.7262	Intermediate Similarity	NPD6926	Approved
0.7253	Intermediate Similarity	NPD3618	Phase 1
0.7241	Intermediate Similarity	NPD4195	Approved
0.7222	Intermediate Similarity	NPD4197	Approved
0.7204	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6933	Approved
0.7065	Intermediate Similarity	NPD5690	Phase 2
0.7053	Intermediate Similarity	NPD6079	Approved
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7041	Intermediate Similarity	NPD7902	Approved
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.701	Intermediate Similarity	NPD5210	Approved
0.701	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.6988	Remote Similarity	NPD6922	Approved
0.6988	Remote Similarity	NPD6923	Approved
0.6979	Remote Similarity	NPD5133	Approved
0.6977	Remote Similarity	NPD8264	Approved
0.6966	Remote Similarity	NPD7525	Registered
0.6957	Remote Similarity	NPD1696	Phase 3
0.6939	Remote Similarity	NPD7614	Phase 1
0.6939	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5221	Approved
0.6939	Remote Similarity	NPD5222	Approved
0.6939	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD4788	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6672	Approved
0.6905	Remote Similarity	NPD7144	Approved
0.6905	Remote Similarity	NPD7143	Approved
0.6869	Remote Similarity	NPD4755	Approved
0.6869	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD4785	Approved
0.686	Remote Similarity	NPD4784	Approved
0.6854	Remote Similarity	NPD6929	Approved
0.6837	Remote Similarity	NPD5695	Phase 3
0.6824	Remote Similarity	NPD7152	Approved
0.6824	Remote Similarity	NPD4243	Approved
0.6824	Remote Similarity	NPD7151	Approved
0.6824	Remote Similarity	NPD7150	Approved
0.6804	Remote Similarity	NPD4202	Approved
0.6778	Remote Similarity	NPD6930	Phase 2
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD7509	Discontinued
0.6735	Remote Similarity	NPD7900	Approved
0.6735	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5286	Approved
0.6733	Remote Similarity	NPD4700	Approved
0.6733	Remote Similarity	NPD4696	Approved
0.6733	Remote Similarity	NPD5285	Approved
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4623	Approved
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD4519	Discontinued
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.6701	Remote Similarity	NPD5284	Approved
0.6701	Remote Similarity	NPD5281	Approved
0.6701	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD5696	Approved
0.6633	Remote Similarity	NPD6399	Phase 3
0.6629	Remote Similarity	NPD6932	Approved
0.6629	Remote Similarity	NPD5776	Phase 2
0.6629	Remote Similarity	NPD6925	Approved
0.6602	Remote Similarity	NPD5211	Phase 2
0.6602	Remote Similarity	NPD5225	Approved
0.6602	Remote Similarity	NPD5226	Approved
0.6602	Remote Similarity	NPD5224	Approved
0.6602	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD7732	Phase 3
0.6598	Remote Similarity	NPD4096	Approved
0.6598	Remote Similarity	NPD5692	Phase 3
0.6593	Remote Similarity	NPD4748	Discontinued
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6562	Remote Similarity	NPD4518	Approved
0.6562	Remote Similarity	NPD6903	Approved
0.6559	Remote Similarity	NPD6695	Phase 3
0.6556	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7145	Approved
0.6538	Remote Similarity	NPD4754	Approved
0.6538	Remote Similarity	NPD5175	Approved
0.6538	Remote Similarity	NPD5174	Approved
0.6531	Remote Similarity	NPD5694	Approved
0.6531	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD8028	Phase 2
0.6512	Remote Similarity	NPD4789	Approved
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6080	Approved
0.6495	Remote Similarity	NPD6904	Approved
0.6489	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6683	Phase 2
0.6477	Remote Similarity	NPD4687	Approved
0.6477	Remote Similarity	NPD4058	Approved
0.6476	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD5290	Discontinued
0.6458	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6899	Approved
0.6437	Remote Similarity	NPD5276	Approved
0.6421	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6893	Approved
0.6415	Remote Similarity	NPD4767	Approved
0.6415	Remote Similarity	NPD4768	Approved
0.6413	Remote Similarity	NPD7332	Phase 2
0.6413	Remote Similarity	NPD7514	Phase 3
0.6408	Remote Similarity	NPD7640	Approved
0.6408	Remote Similarity	NPD7639	Approved
0.6404	Remote Similarity	NPD5275	Approved
0.6404	Remote Similarity	NPD4190	Phase 3
0.6395	Remote Similarity	NPD4137	Phase 3
0.6389	Remote Similarity	NPD6373	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6355	Remote Similarity	NPD6412	Phase 2
0.6355	Remote Similarity	NPD5697	Approved
0.6354	Remote Similarity	NPD6098	Approved
0.6344	Remote Similarity	NPD4692	Approved
0.6344	Remote Similarity	NPD6902	Approved
0.6344	Remote Similarity	NPD4139	Approved
0.6344	Remote Similarity	NPD6898	Phase 1
0.6337	Remote Similarity	NPD5654	Approved
0.633	Remote Similarity	NPD7290	Approved
0.633	Remote Similarity	NPD6883	Approved
0.633	Remote Similarity	NPD7102	Approved
0.6327	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6101	Approved
0.6322	Remote Similarity	NPD4691	Approved
0.6322	Remote Similarity	NPD4747	Approved
0.6296	Remote Similarity	NPD4729	Approved
0.6296	Remote Similarity	NPD4730	Approved
0.6296	Remote Similarity	NPD5168	Approved
0.6296	Remote Similarity	NPD6011	Approved
0.6296	Remote Similarity	NPD5128	Approved
0.6289	Remote Similarity	NPD3573	Approved
0.6289	Remote Similarity	NPD7750	Discontinued
0.6289	Remote Similarity	NPD7524	Approved
0.6273	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6617	Approved
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6847	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.6273	Remote Similarity	NPD6869	Approved
0.6273	Remote Similarity	NPD8130	Phase 1
0.6263	Remote Similarity	NPD5207	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6216	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD8297	Approved
0.6214	Remote Similarity	NPD5959	Approved
0.62	Remote Similarity	NPD5693	Phase 1
0.6182	Remote Similarity	NPD5249	Phase 3
0.6182	Remote Similarity	NPD5248	Approved
0.6182	Remote Similarity	NPD5247	Approved
0.6182	Remote Similarity	NPD5250	Approved
0.6182	Remote Similarity	NPD4634	Approved
0.6182	Remote Similarity	NPD5251	Approved
0.6182	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5169	Approved
0.6182	Remote Similarity	NPD5135	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