NPASS Compound

Structure

NPC474493 OpenBabel07101718242D 32 35 0 0 1 0 0 0 0 0999 V2000 5.2964 -4.8258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4232 -3.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1289 -2.8742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1978 2.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1700 2.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4064 -2.2236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2885 -1.8604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9782 -2.2733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7761 -3.2243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2557 -1.6228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6086 0.3004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1800 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4986 -3.8748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3311 -1.9232 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5259 1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6086 -1.2727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 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 -3.3679 1.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -0.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 21 3 1 1 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 1 0 0 0 24 26 1 0 0 0 0 24 29 1 6 0 0 0 25 26 1 0 0 0 0 25 31 1 1 0 0 0 27 28 1 1 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	6.835
LogD:	4.925
LogS:	-5.898
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	5.213
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	1.4324997209769208e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.372
Plasma Protein Binding (PPB):	96.1643295288086%
Volume Distribution (VD):	1.33
Pgp-substrate:	2.576504945755005%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.29
CYP2C19-inhibitor:	0.291
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.404
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.59
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	11.748
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.291
Human Hepatotoxicity (H-HT):	0.421
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.39
Carcinogencity:	0.406
Eye Corrosion:	0.058
Eye Irritation:	0.035
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC474493

Natural Product ID:	NPC474493
*Common Name:**	Garcihombronane F
IUPAC Name:	(3R,5S,8S,9R,10S,13S,17S)-4,4,10,13,17-pentamethyl-17-[(2R,3Z)-6-methylhepta-3,5-dien-2-yl]-1,2,3,5,6,7,8,11,12,16-decahydrocyclopenta[a]phenanthrene-3,9-diol
Synonyms:	garcihombronane F
Standard InCHIKey:	AAAKMEGSCBCTHX-OUWACTBKSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-20(2)10-9-11-21(3)27(6)16-14-22-23-12-13-24-26(4,5)25(31)15-17-29(24,8)30(23,32)19-18-28(22,27)7/h9-11,14,21,23-25,31-32H,12-13,15-19H2,1-8H3/b11-9-/t21-,23+,24+,25-,27+,28-,29+,30-/m1/s1
SMILES:	CC(C=CC=C(C)C)C1(CC=C2C1(CCC3(C2CCC4C3(CCC(C4(C)C)O)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470033
PubChem CID:	44559176
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

*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
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[459593]

☑ 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 NPC474493 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	184
0.1-0.2	1305
0.2-0.3	5042
0.3-0.4	14939
0.4-0.5	9939
0.5-0.6	6094
0.6-0.7	3920
0.7-0.8	1113
0.8-0.85	140
0.85-0.9	17
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC472463
0.925	High Similarity	NPC248886
0.8987	High Similarity	NPC285761
0.8987	High Similarity	NPC148977
0.8902	High Similarity	NPC477818
0.8875	High Similarity	NPC80530
0.8875	High Similarity	NPC273410
0.8861	High Similarity	NPC471798
0.881	High Similarity	NPC261266
0.8795	High Similarity	NPC209802
0.8795	High Similarity	NPC127606
0.8795	High Similarity	NPC475798
0.878	High Similarity	NPC218616
0.878	High Similarity	NPC296701
0.8765	High Similarity	NPC13554
0.8765	High Similarity	NPC322313
0.8765	High Similarity	NPC236237
0.8765	High Similarity	NPC102253
0.875	High Similarity	NPC18603
0.875	High Similarity	NPC307965
0.875	High Similarity	NPC167037
0.875	High Similarity	NPC318136
0.875	High Similarity	NPC76931
0.875	High Similarity	NPC244385
0.875	High Similarity	NPC312328
0.875	High Similarity	NPC138621
0.875	High Similarity	NPC6978
0.875	High Similarity	NPC87604
0.8734	High Similarity	NPC237460
0.8675	High Similarity	NPC141941
0.8675	High Similarity	NPC193870
0.8675	High Similarity	NPC110778
0.8675	High Similarity	NPC113978
0.8659	High Similarity	NPC470383
0.8625	High Similarity	NPC155986
0.8625	High Similarity	NPC198968
0.8625	High Similarity	NPC318495
0.8608	High Similarity	NPC103822
0.8605	High Similarity	NPC470542
0.8588	High Similarity	NPC94462
0.8588	High Similarity	NPC6391
0.8588	High Similarity	NPC6605
0.8588	High Similarity	NPC24277
0.8588	High Similarity	NPC201273
0.8571	High Similarity	NPC124172
0.8571	High Similarity	NPC231310
0.8571	High Similarity	NPC238485
0.8554	High Similarity	NPC50964
0.8554	High Similarity	NPC201852
0.8554	High Similarity	NPC49964
0.8537	High Similarity	NPC164840
0.8537	High Similarity	NPC241290
0.8537	High Similarity	NPC26117
0.8537	High Similarity	NPC209944
0.8519	High Similarity	NPC302041
0.8519	High Similarity	NPC85346
0.8519	High Similarity	NPC205455
0.8519	High Similarity	NPC186191
0.8519	High Similarity	NPC11908
0.8519	High Similarity	NPC275910
0.8519	High Similarity	NPC31828
0.8519	High Similarity	NPC65897
0.85	High Similarity	NPC113733
0.85	High Similarity	NPC134330
0.85	High Similarity	NPC321381
0.85	High Similarity	NPC189883
0.85	High Similarity	NPC321016
0.85	High Similarity	NPC106432
0.85	High Similarity	NPC240604
0.85	High Similarity	NPC129165
0.85	High Similarity	NPC107059
0.85	High Similarity	NPC300324
0.8481	Intermediate Similarity	NPC329090
0.8481	Intermediate Similarity	NPC243342
0.8481	Intermediate Similarity	NPC472503
0.8481	Intermediate Similarity	NPC477138
0.8481	Intermediate Similarity	NPC308440
0.8481	Intermediate Similarity	NPC27395
0.8471	Intermediate Similarity	NPC470360
0.8462	Intermediate Similarity	NPC167706
0.8452	Intermediate Similarity	NPC237795
0.8452	Intermediate Similarity	NPC134481
0.8452	Intermediate Similarity	NPC470558
0.8452	Intermediate Similarity	NPC82623
0.8452	Intermediate Similarity	NPC82538
0.8452	Intermediate Similarity	NPC207013
0.8434	Intermediate Similarity	NPC476646
0.8434	Intermediate Similarity	NPC47761
0.8434	Intermediate Similarity	NPC23852
0.8434	Intermediate Similarity	NPC474531
0.8434	Intermediate Similarity	NPC264245
0.8434	Intermediate Similarity	NPC6707
0.8434	Intermediate Similarity	NPC209620
0.8427	Intermediate Similarity	NPC310013
0.8415	Intermediate Similarity	NPC328714
0.8415	Intermediate Similarity	NPC1319
0.8415	Intermediate Similarity	NPC291379
0.8409	Intermediate Similarity	NPC295668
0.8409	Intermediate Similarity	NPC329596
0.8409	Intermediate Similarity	NPC11216
0.8409	Intermediate Similarity	NPC473956
0.8409	Intermediate Similarity	NPC291484
0.8409	Intermediate Similarity	NPC204188
0.8409	Intermediate Similarity	NPC475751
0.8409	Intermediate Similarity	NPC80561
0.8409	Intermediate Similarity	NPC3345
0.8395	Intermediate Similarity	NPC214570
0.8395	Intermediate Similarity	NPC202540
0.8395	Intermediate Similarity	NPC470711
0.8395	Intermediate Similarity	NPC470758
0.8391	Intermediate Similarity	NPC475664
0.8391	Intermediate Similarity	NPC193360
0.8391	Intermediate Similarity	NPC133588
0.8375	Intermediate Similarity	NPC328104
0.8375	Intermediate Similarity	NPC257347
0.8375	Intermediate Similarity	NPC230301
0.8375	Intermediate Similarity	NPC304309
0.8375	Intermediate Similarity	NPC288035
0.8375	Intermediate Similarity	NPC3403
0.8375	Intermediate Similarity	NPC162742
0.8375	Intermediate Similarity	NPC22105
0.8375	Intermediate Similarity	NPC285893
0.8375	Intermediate Similarity	NPC319090
0.8375	Intermediate Similarity	NPC134847
0.8375	Intermediate Similarity	NPC141071
0.8375	Intermediate Similarity	NPC291503
0.8375	Intermediate Similarity	NPC28657
0.8375	Intermediate Similarity	NPC136188
0.8375	Intermediate Similarity	NPC471723
0.8372	Intermediate Similarity	NPC269058
0.8372	Intermediate Similarity	NPC299068
0.8372	Intermediate Similarity	NPC139724
0.8372	Intermediate Similarity	NPC71520
0.8354	Intermediate Similarity	NPC471799
0.8354	Intermediate Similarity	NPC182717
0.8354	Intermediate Similarity	NPC68443
0.8353	Intermediate Similarity	NPC470077
0.8353	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC470614
0.8333	Intermediate Similarity	NPC1272
0.8333	Intermediate Similarity	NPC20853
0.8333	Intermediate Similarity	NPC30166
0.8333	Intermediate Similarity	NPC87489
0.8333	Intermediate Similarity	NPC202389
0.8333	Intermediate Similarity	NPC209662
0.8315	Intermediate Similarity	NPC41554
0.8315	Intermediate Similarity	NPC97404
0.8313	Intermediate Similarity	NPC96362
0.8313	Intermediate Similarity	NPC236112
0.8313	Intermediate Similarity	NPC78545
0.8313	Intermediate Similarity	NPC234193
0.8313	Intermediate Similarity	NPC287749
0.8313	Intermediate Similarity	NPC324772
0.8313	Intermediate Similarity	NPC71535
0.8295	Intermediate Similarity	NPC109744
0.8295	Intermediate Similarity	NPC105495
0.8295	Intermediate Similarity	NPC101886
0.8295	Intermediate Similarity	NPC470361
0.8293	Intermediate Similarity	NPC470396
0.8293	Intermediate Similarity	NPC473943
0.8293	Intermediate Similarity	NPC474989
0.8293	Intermediate Similarity	NPC477819
0.8293	Intermediate Similarity	NPC477817
0.8293	Intermediate Similarity	NPC72507
0.8293	Intermediate Similarity	NPC22955
0.8293	Intermediate Similarity	NPC477522
0.8293	Intermediate Similarity	NPC99168
0.8293	Intermediate Similarity	NPC474216
0.8276	Intermediate Similarity	NPC474657
0.8276	Intermediate Similarity	NPC271967
0.8276	Intermediate Similarity	NPC186145
0.8272	Intermediate Similarity	NPC265588
0.8272	Intermediate Similarity	NPC63958
0.8272	Intermediate Similarity	NPC91573
0.8272	Intermediate Similarity	NPC202642
0.8272	Intermediate Similarity	NPC470362
0.8272	Intermediate Similarity	NPC470749
0.8272	Intermediate Similarity	NPC73875
0.8272	Intermediate Similarity	NPC46160
0.8272	Intermediate Similarity	NPC315261
0.8256	Intermediate Similarity	NPC318390
0.8256	Intermediate Similarity	NPC274448
0.8256	Intermediate Similarity	NPC157257
0.825	Intermediate Similarity	NPC100334
0.825	Intermediate Similarity	NPC91858
0.825	Intermediate Similarity	NPC471797
0.8235	Intermediate Similarity	NPC470384
0.8235	Intermediate Similarity	NPC232023
0.8228	Intermediate Similarity	NPC242001
0.8228	Intermediate Similarity	NPC111234
0.8214	Intermediate Similarity	NPC242350
0.8214	Intermediate Similarity	NPC320525
0.8214	Intermediate Similarity	NPC249423
0.8205	Intermediate Similarity	NPC476431
0.8205	Intermediate Similarity	NPC210323
0.8202	Intermediate Similarity	NPC245410
0.8202	Intermediate Similarity	NPC470390
0.8202	Intermediate Similarity	NPC192437
0.8202	Intermediate Similarity	NPC270511
0.8202	Intermediate Similarity	NPC14380

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 NPC474493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1415
0.2-0.3	4030
0.3-0.4	2415
0.4-0.5	704
0.5-0.6	207
0.6-0.7	154
0.7-0.8	42
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD7525	Registered
0.8481	Intermediate Similarity	NPD6926	Approved
0.8481	Intermediate Similarity	NPD6924	Approved
0.8395	Intermediate Similarity	NPD6932	Approved
0.8375	Intermediate Similarity	NPD7339	Approved
0.8375	Intermediate Similarity	NPD6942	Approved
0.8313	Intermediate Similarity	NPD7509	Discontinued
0.8313	Intermediate Similarity	NPD6931	Approved
0.8313	Intermediate Similarity	NPD6930	Phase 2
0.8313	Intermediate Similarity	NPD7332	Phase 2
0.8272	Intermediate Similarity	NPD6933	Approved
0.8228	Intermediate Similarity	NPD7151	Approved
0.8228	Intermediate Similarity	NPD7150	Approved
0.8228	Intermediate Similarity	NPD7152	Approved
0.8193	Intermediate Similarity	NPD6929	Approved
0.8101	Intermediate Similarity	NPD7143	Approved
0.8101	Intermediate Similarity	NPD7144	Approved
0.8095	Intermediate Similarity	NPD7514	Phase 3
0.8072	Intermediate Similarity	NPD7145	Approved
0.8072	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6695	Phase 3
0.8	Intermediate Similarity	NPD6898	Phase 1
0.7976	Intermediate Similarity	NPD7645	Phase 2
0.7976	Intermediate Similarity	NPD6683	Phase 2
0.7975	Intermediate Similarity	NPD6923	Approved
0.7975	Intermediate Similarity	NPD6922	Approved
0.7952	Intermediate Similarity	NPD6925	Approved
0.7952	Intermediate Similarity	NPD5776	Phase 2
0.7931	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6893	Approved
0.7805	Intermediate Similarity	NPD4785	Approved
0.7805	Intermediate Similarity	NPD4784	Approved
0.7791	Intermediate Similarity	NPD6902	Approved
0.7727	Intermediate Similarity	NPD4786	Approved
0.7667	Intermediate Similarity	NPD7524	Approved
0.7667	Intermediate Similarity	NPD7750	Discontinued
0.7561	Intermediate Similarity	NPD4243	Approved
0.7527	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD8264	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7471	Intermediate Similarity	NPD4748	Discontinued
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.734	Intermediate Similarity	NPD7087	Discontinued
0.7263	Intermediate Similarity	NPD4202	Approved
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7638	Approved
0.7234	Intermediate Similarity	NPD7136	Phase 2
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7159	Intermediate Similarity	NPD4195	Approved
0.7108	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4190	Phase 3
0.7093	Intermediate Similarity	NPD5275	Approved
0.7041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5222	Approved
0.7041	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6989	Remote Similarity	NPD5279	Phase 3
0.6979	Remote Similarity	NPD7515	Phase 2
0.6979	Remote Similarity	NPD7637	Suspended
0.697	Remote Similarity	NPD4755	Approved
0.697	Remote Similarity	NPD5173	Approved
0.6957	Remote Similarity	NPD3665	Phase 1
0.6957	Remote Similarity	NPD3666	Approved
0.6957	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD6399	Phase 3
0.6869	Remote Similarity	NPD4697	Phase 3
0.6863	Remote Similarity	NPD5224	Approved
0.6863	Remote Similarity	NPD5211	Phase 2
0.6863	Remote Similarity	NPD4633	Approved
0.6863	Remote Similarity	NPD5225	Approved
0.6863	Remote Similarity	NPD5226	Approved
0.6848	Remote Similarity	NPD4788	Approved
0.6832	Remote Similarity	NPD4700	Approved
0.6824	Remote Similarity	NPD4787	Phase 1
0.6796	Remote Similarity	NPD5174	Approved
0.6796	Remote Similarity	NPD5175	Approved
0.6774	Remote Similarity	NPD3668	Phase 3
0.6771	Remote Similarity	NPD4753	Phase 2
0.6739	Remote Similarity	NPD4221	Approved
0.6739	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD5290	Discontinued
0.6731	Remote Similarity	NPD5141	Approved
0.6729	Remote Similarity	NPD4634	Approved
0.6702	Remote Similarity	NPD5329	Approved
0.6698	Remote Similarity	NPD6881	Approved
0.6698	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6635	Remote Similarity	NPD4754	Approved
0.6633	Remote Similarity	NPD8034	Phase 2
0.6633	Remote Similarity	NPD8035	Phase 2
0.6632	Remote Similarity	NPD4694	Approved
0.6632	Remote Similarity	NPD5280	Approved
0.6604	Remote Similarity	NPD5697	Approved
0.66	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD5210	Approved
0.6596	Remote Similarity	NPD4197	Approved
0.6574	Remote Similarity	NPD6883	Approved
0.6574	Remote Similarity	NPD7290	Approved
0.6574	Remote Similarity	NPD7102	Approved
0.6552	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD6011	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD4730	Approved
0.6542	Remote Similarity	NPD4729	Approved
0.6538	Remote Similarity	NPD7632	Discontinued
0.6517	Remote Similarity	NPD3703	Phase 2
0.6514	Remote Similarity	NPD6649	Approved
0.6514	Remote Similarity	NPD6869	Approved
0.6514	Remote Similarity	NPD6617	Approved
0.6514	Remote Similarity	NPD6847	Approved
0.6514	Remote Similarity	NPD6650	Approved
0.6514	Remote Similarity	NPD8130	Phase 1
0.6509	Remote Similarity	NPD4767	Approved
0.6509	Remote Similarity	NPD4768	Approved
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6012	Approved
0.6481	Remote Similarity	NPD6013	Approved
0.6481	Remote Similarity	NPD6014	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6477	Remote Similarity	NPD4732	Discontinued
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD7902	Approved
0.6465	Remote Similarity	NPD5281	Approved
0.6465	Remote Similarity	NPD6411	Approved
0.6465	Remote Similarity	NPD5284	Approved
0.646	Remote Similarity	NPD7328	Approved
0.646	Remote Similarity	NPD7327	Approved
0.6458	Remote Similarity	NPD4519	Discontinued
0.6458	Remote Similarity	NPD5690	Phase 2
0.6458	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4688	Approved
0.6458	Remote Similarity	NPD4689	Approved
0.6458	Remote Similarity	NPD4623	Approved
0.6458	Remote Similarity	NPD4138	Approved
0.6458	Remote Similarity	NPD5205	Approved
0.6458	Remote Similarity	NPD4693	Phase 3
0.6458	Remote Similarity	NPD4690	Approved
0.6455	Remote Similarity	NPD6882	Approved
0.6455	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD5701	Approved
0.6444	Remote Similarity	NPD6117	Approved
0.6435	Remote Similarity	NPD7503	Approved
0.6435	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD6051	Approved
0.6422	Remote Similarity	NPD5169	Approved
0.6422	Remote Similarity	NPD5251	Approved
0.6422	Remote Similarity	NPD5249	Phase 3
0.6422	Remote Similarity	NPD5135	Approved
0.6422	Remote Similarity	NPD5247	Approved
0.6422	Remote Similarity	NPD5248	Approved
0.6422	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5250	Approved
0.6404	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7516	Approved
0.6389	Remote Similarity	NPD5128	Approved
0.6389	Remote Similarity	NPD5168	Approved
0.6374	Remote Similarity	NPD6116	Phase 1
0.6372	Remote Similarity	NPD6009	Approved
0.6372	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5217	Approved
0.6364	Remote Similarity	NPD5127	Approved
0.6364	Remote Similarity	NPD5215	Approved
0.6364	Remote Similarity	NPD5216	Approved
0.6355	Remote Similarity	NPD6640	Phase 3
0.6355	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD1696	Phase 3
0.6348	Remote Similarity	NPD7741	Discontinued
0.6348	Remote Similarity	NPD8377	Approved
0.6348	Remote Similarity	NPD6054	Approved
0.6348	Remote Similarity	NPD8294	Approved
0.6344	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6928	Phase 2
0.6327	Remote Similarity	NPD4723	Approved
0.6327	Remote Similarity	NPD4722	Approved
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4518	Approved
0.6322	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8335	Approved
0.6293	Remote Similarity	NPD8378	Approved
0.6293	Remote Similarity	NPD8380	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