NPASS Compound

Structure

NPC158846 OpenBabel07101718282D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5446 4.7859 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 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 -2.6831 -0.3090 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 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 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 -2.9921 2.2601 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 -2.6831 1.3090 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 3 21 2 0 0 0 0 4 21 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 21 23 1 0 0 0 0 22 5 1 1 0 0 0 22 24 1 0 0 0 0 23 29 1 6 0 0 0 24 27 1 6 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	7.761
LogD:	5.519
LogS:	-5.994
# Rotatable Bonds:	8
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	5.271
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.117
MDCK Permeability:	6.834267878730316e-06
Pgp-inhibitor:	0.017
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	96.15125274658203%
Volume Distribution (VD):	0.735
Pgp-substrate:	2.3234481811523438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.26
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	9.42
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.39
Human Hepatotoxicity (H-HT):	0.643
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.12
Skin Sensitization:	0.94
Carcinogencity:	0.264
Eye Corrosion:	0.056
Eye Irritation:	0.165
Respiratory Toxicity:	0.794

Download Data

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

Natural Product: NPC158846

Natural Product ID:	NPC158846
*Common Name:**	Sootepin E
IUPAC Name:	n.a.
Synonyms:	Sootepin E
Standard InCHIKey:	KNVUFXYCGYEIRS-DZWGBXGJSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-20(2)9-8-10-22(5)24-13-15-28(7)25-12-11-23(21(3)4)29(16-14-26(31)32)19-30(25,29)18-17-27(24,28)6/h9,22-25H,3,8,10-19H2,1-2,4-7H3,(H,31,32)/t22-,23+,24-,25+,27-,28+,29-,30+/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(=C)C)[C@@]4(CCC(=O)O)C[C@@]34CC[C@]12C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557656
PubChem CID:	44179870
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO11647	Gardenia sootepensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19456120]
NPO33315	gardenia spp.	Species	Rubiaceae	Eukaryota	n.a.	Thai	n.a.	PMID[22142538]
NPO11647	Gardenia sootepensis	Species	Rubiaceae	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	5
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3.14	ug.mL-1	PMID[449645]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	4.22	ug.mL-1	PMID[449645]
NPT845	Cell Line	BT-474	Homo sapiens	IC50	=	6.07	ug.mL-1	PMID[449645]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.91	ug.mL-1	PMID[449645]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.2	ug.mL-1	PMID[449645]
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	=	92.0	%	PMID[449646]

☑ 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 NPC158846 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	146
0.1-0.2	1202
0.2-0.3	7732
0.3-0.4	15434
0.4-0.5	6422
0.5-0.6	6665
0.6-0.7	3950
0.7-0.8	1019
0.8-0.85	94
0.85-0.9	18
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC476038
0.9359	High Similarity	NPC194937
0.9241	High Similarity	NPC283733
0.9221	High Similarity	NPC147066
0.9211	High Similarity	NPC477371
0.9125	High Similarity	NPC186975
0.9079	High Similarity	NPC321690
0.9067	High Similarity	NPC20466
0.9012	High Similarity	NPC236618
0.8987	High Similarity	NPC167103
0.8974	High Similarity	NPC477372
0.8974	High Similarity	NPC38350
0.8974	High Similarity	NPC201912
0.8902	High Similarity	NPC117122
0.8861	High Similarity	NPC133391
0.8861	High Similarity	NPC260956
0.8861	High Similarity	NPC320514
0.8816	High Similarity	NPC246445
0.8795	High Similarity	NPC66344
0.8795	High Similarity	NPC128496
0.8784	High Similarity	NPC160817
0.8765	High Similarity	NPC269638
0.8765	High Similarity	NPC29447
0.875	High Similarity	NPC69279
0.875	High Similarity	NPC477373
0.875	High Similarity	NPC83569
0.8718	High Similarity	NPC196827
0.8718	High Similarity	NPC274996
0.8718	High Similarity	NPC215843
0.8701	High Similarity	NPC66105
0.8701	High Similarity	NPC107039
0.8701	High Similarity	NPC471897
0.8701	High Similarity	NPC68828
0.8701	High Similarity	NPC471899
0.8684	High Similarity	NPC192540
0.8684	High Similarity	NPC279666
0.8684	High Similarity	NPC476844
0.8667	High Similarity	NPC330659
0.8667	High Similarity	NPC244708
0.8667	High Similarity	NPC161187
0.8659	High Similarity	NPC155011
0.8642	High Similarity	NPC19849
0.8642	High Similarity	NPC164577
0.8642	High Similarity	NPC165064
0.8642	High Similarity	NPC472864
0.859	High Similarity	NPC110094
0.859	High Similarity	NPC280654
0.859	High Similarity	NPC260385
0.8588	High Similarity	NPC470113
0.8588	High Similarity	NPC476187
0.8571	High Similarity	NPC89294
0.8571	High Similarity	NPC69143
0.8554	High Similarity	NPC136948
0.8554	High Similarity	NPC128644
0.8554	High Similarity	NPC96496
0.8554	High Similarity	NPC474684
0.8554	High Similarity	NPC142361
0.8553	High Similarity	NPC251970
0.8553	High Similarity	NPC241854
0.8553	High Similarity	NPC283908
0.8553	High Similarity	NPC183503
0.8553	High Similarity	NPC237591
0.8553	High Similarity	NPC103958
0.8553	High Similarity	NPC3753
0.8553	High Similarity	NPC161923
0.8553	High Similarity	NPC476046
0.8519	High Similarity	NPC477852
0.8519	High Similarity	NPC97913
0.8481	Intermediate Similarity	NPC16394
0.8481	Intermediate Similarity	NPC231431
0.8481	Intermediate Similarity	NPC199595
0.8481	Intermediate Similarity	NPC192744
0.8442	Intermediate Similarity	NPC201027
0.8434	Intermediate Similarity	NPC472869
0.8415	Intermediate Similarity	NPC472865
0.8395	Intermediate Similarity	NPC296367
0.8391	Intermediate Similarity	NPC124207
0.8378	Intermediate Similarity	NPC290445
0.8378	Intermediate Similarity	NPC36616
0.8375	Intermediate Similarity	NPC37038
0.8375	Intermediate Similarity	NPC104545
0.8354	Intermediate Similarity	NPC179028
0.8354	Intermediate Similarity	NPC239098
0.8354	Intermediate Similarity	NPC321514
0.8353	Intermediate Similarity	NPC475921
0.8353	Intermediate Similarity	NPC262043
0.8353	Intermediate Similarity	NPC474704
0.8353	Intermediate Similarity	NPC474570
0.8333	Intermediate Similarity	NPC187376
0.8333	Intermediate Similarity	NPC159046
0.8333	Intermediate Similarity	NPC309399
0.8333	Intermediate Similarity	NPC233836
0.8333	Intermediate Similarity	NPC167877
0.8312	Intermediate Similarity	NPC301065
0.8295	Intermediate Similarity	NPC476174
0.8295	Intermediate Similarity	NPC293052
0.8293	Intermediate Similarity	NPC168188
0.8293	Intermediate Similarity	NPC310470
0.8293	Intermediate Similarity	NPC470015
0.8293	Intermediate Similarity	NPC215893
0.8276	Intermediate Similarity	NPC477855
0.8272	Intermediate Similarity	NPC267691
0.8272	Intermediate Similarity	NPC162632
0.8272	Intermediate Similarity	NPC278459
0.8272	Intermediate Similarity	NPC274050
0.8272	Intermediate Similarity	NPC263272
0.8272	Intermediate Similarity	NPC232625
0.8272	Intermediate Similarity	NPC221647
0.8272	Intermediate Similarity	NPC142244
0.8272	Intermediate Similarity	NPC471898
0.8256	Intermediate Similarity	NPC471896
0.825	Intermediate Similarity	NPC327674
0.8235	Intermediate Similarity	NPC472870
0.8228	Intermediate Similarity	NPC61952
0.8228	Intermediate Similarity	NPC238227
0.8228	Intermediate Similarity	NPC165711
0.8228	Intermediate Similarity	NPC471035
0.8228	Intermediate Similarity	NPC212661
0.8214	Intermediate Similarity	NPC55309
0.8214	Intermediate Similarity	NPC475007
0.8214	Intermediate Similarity	NPC70661
0.8214	Intermediate Similarity	NPC28252
0.8205	Intermediate Similarity	NPC476795
0.8202	Intermediate Similarity	NPC327788
0.8202	Intermediate Similarity	NPC29152
0.8193	Intermediate Similarity	NPC85774
0.8193	Intermediate Similarity	NPC178025
0.8193	Intermediate Similarity	NPC16287
0.8193	Intermediate Similarity	NPC59453
0.8193	Intermediate Similarity	NPC221758
0.8193	Intermediate Similarity	NPC82902
0.8193	Intermediate Similarity	NPC248758
0.8193	Intermediate Similarity	NPC214043
0.8193	Intermediate Similarity	NPC181743
0.8182	Intermediate Similarity	NPC36310
0.8182	Intermediate Similarity	NPC279241
0.8171	Intermediate Similarity	NPC240302
0.8171	Intermediate Similarity	NPC69101
0.8171	Intermediate Similarity	NPC193347
0.8171	Intermediate Similarity	NPC251779
0.8161	Intermediate Similarity	NPC154101
0.8161	Intermediate Similarity	NPC189520
0.8158	Intermediate Similarity	NPC91369
0.8148	Intermediate Similarity	NPC477057
0.814	Intermediate Similarity	NPC84271
0.814	Intermediate Similarity	NPC215029
0.814	Intermediate Similarity	NPC102414
0.814	Intermediate Similarity	NPC476733
0.814	Intermediate Similarity	NPC77168
0.8125	Intermediate Similarity	NPC198240
0.8125	Intermediate Similarity	NPC59436
0.8118	Intermediate Similarity	NPC312215
0.8111	Intermediate Similarity	NPC156546
0.8101	Intermediate Similarity	NPC180886
0.8095	Intermediate Similarity	NPC142649
0.8095	Intermediate Similarity	NPC311702
0.8095	Intermediate Similarity	NPC471224
0.8095	Intermediate Similarity	NPC474218
0.8095	Intermediate Similarity	NPC60350
0.8095	Intermediate Similarity	NPC202868
0.8095	Intermediate Similarity	NPC123319
0.8095	Intermediate Similarity	NPC469948
0.8095	Intermediate Similarity	NPC470223
0.8095	Intermediate Similarity	NPC94531
0.8077	Intermediate Similarity	NPC18819
0.8077	Intermediate Similarity	NPC166797
0.8077	Intermediate Similarity	NPC46610
0.8077	Intermediate Similarity	NPC255168
0.8072	Intermediate Similarity	NPC245866
0.8072	Intermediate Similarity	NPC472740
0.8072	Intermediate Similarity	NPC70834
0.8072	Intermediate Similarity	NPC200752
0.8068	Intermediate Similarity	NPC470375
0.8068	Intermediate Similarity	NPC470224
0.8068	Intermediate Similarity	NPC470376
0.8052	Intermediate Similarity	NPC72343
0.8049	Intermediate Similarity	NPC327002
0.8049	Intermediate Similarity	NPC14203
0.8049	Intermediate Similarity	NPC40228
0.8049	Intermediate Similarity	NPC229584
0.8046	Intermediate Similarity	NPC148414
0.8046	Intermediate Similarity	NPC111585
0.8046	Intermediate Similarity	NPC175628
0.8046	Intermediate Similarity	NPC472866
0.8023	Intermediate Similarity	NPC242864
0.8023	Intermediate Similarity	NPC146937
0.8023	Intermediate Similarity	NPC294480
0.8022	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC474732
0.8	Intermediate Similarity	NPC51014
0.8	Intermediate Similarity	NPC130459
0.8	Intermediate Similarity	NPC474778
0.8	Intermediate Similarity	NPC478180
0.8	Intermediate Similarity	NPC474221
0.8	Intermediate Similarity	NPC212843
0.8	Intermediate Similarity	NPC469994
0.8	Intermediate Similarity	NPC6247
0.8	Intermediate Similarity	NPC264127
0.8	Intermediate Similarity	NPC31564
0.8	Intermediate Similarity	NPC474733

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 NPC158846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1556
0.2-0.3	4334
0.3-0.4	2093
0.4-0.5	554
0.5-0.6	199
0.6-0.7	176
0.7-0.8	92
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8193	Intermediate Similarity	NPD4786	Approved
0.8171	Intermediate Similarity	NPD4221	Approved
0.8171	Intermediate Similarity	NPD4223	Phase 3
0.8095	Intermediate Similarity	NPD5329	Approved
0.8068	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD6098	Approved
0.7976	Intermediate Similarity	NPD4197	Approved
0.7952	Intermediate Similarity	NPD3667	Approved
0.7882	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6672	Approved
0.7816	Intermediate Similarity	NPD5737	Approved
0.7791	Intermediate Similarity	NPD4693	Phase 3
0.7791	Intermediate Similarity	NPD4138	Approved
0.7791	Intermediate Similarity	NPD4690	Approved
0.7791	Intermediate Similarity	NPD6409	Approved
0.7791	Intermediate Similarity	NPD7521	Approved
0.7791	Intermediate Similarity	NPD7334	Approved
0.7791	Intermediate Similarity	NPD7146	Approved
0.7791	Intermediate Similarity	NPD4688	Approved
0.7791	Intermediate Similarity	NPD6684	Approved
0.7791	Intermediate Similarity	NPD4689	Approved
0.7791	Intermediate Similarity	NPD5205	Approved
0.7791	Intermediate Similarity	NPD5330	Approved
0.7765	Intermediate Similarity	NPD3665	Phase 1
0.7765	Intermediate Similarity	NPD3666	Approved
0.7765	Intermediate Similarity	NPD3133	Approved
0.7753	Intermediate Similarity	NPD5284	Approved
0.7753	Intermediate Similarity	NPD5281	Approved
0.7727	Intermediate Similarity	NPD5328	Approved
0.7727	Intermediate Similarity	NPD6080	Approved
0.7727	Intermediate Similarity	NPD6904	Approved
0.7727	Intermediate Similarity	NPD6673	Approved
0.7717	Intermediate Similarity	NPD6084	Phase 2
0.7717	Intermediate Similarity	NPD6083	Phase 2
0.7692	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3617	Approved
0.7614	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6903	Approved
0.7614	Intermediate Similarity	NPD5208	Approved
0.7595	Intermediate Similarity	NPD4243	Approved
0.7586	Intermediate Similarity	NPD3618	Phase 1
0.7586	Intermediate Similarity	NPD5690	Phase 2
0.7586	Intermediate Similarity	NPD4694	Approved
0.7586	Intermediate Similarity	NPD5280	Approved
0.7582	Intermediate Similarity	NPD6001	Approved
0.7556	Intermediate Similarity	NPD6079	Approved
0.7528	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD5695	Phase 3
0.7468	Intermediate Similarity	NPD4747	Approved
0.7447	Intermediate Similarity	NPD5696	Approved
0.7442	Intermediate Similarity	NPD4788	Approved
0.7412	Intermediate Similarity	NPD4692	Approved
0.7412	Intermediate Similarity	NPD4139	Approved
0.7407	Intermediate Similarity	NPD4784	Approved
0.7407	Intermediate Similarity	NPD4785	Approved
0.7403	Intermediate Similarity	NPD4224	Phase 2
0.7386	Intermediate Similarity	NPD5279	Phase 3
0.7386	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4195	Approved
0.7375	Intermediate Similarity	NPD6081	Approved
0.7368	Intermediate Similarity	NPD6404	Discontinued
0.7363	Intermediate Similarity	NPD6050	Approved
0.7363	Intermediate Similarity	NPD7515	Phase 2
0.7363	Intermediate Similarity	NPD8034	Phase 2
0.7363	Intermediate Similarity	NPD5693	Phase 1
0.7363	Intermediate Similarity	NPD8035	Phase 2
0.7356	Intermediate Similarity	NPD3668	Phase 3
0.7342	Intermediate Similarity	NPD4137	Phase 3
0.7333	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6942	Approved
0.7317	Intermediate Similarity	NPD7339	Approved
0.7294	Intermediate Similarity	NPD4695	Discontinued
0.7283	Intermediate Similarity	NPD5133	Approved
0.7283	Intermediate Similarity	NPD4202	Approved
0.7262	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5207	Approved
0.7253	Intermediate Similarity	NPD5692	Phase 3
0.725	Intermediate Similarity	NPD4691	Approved
0.7215	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7748	Approved
0.7195	Intermediate Similarity	NPD6924	Approved
0.7195	Intermediate Similarity	NPD5733	Approved
0.7195	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6926	Approved
0.7191	Intermediate Similarity	NPD4623	Approved
0.7191	Intermediate Similarity	NPD4519	Discontinued
0.7174	Intermediate Similarity	NPD5694	Approved
0.7172	Intermediate Similarity	NPD6675	Approved
0.7172	Intermediate Similarity	NPD6402	Approved
0.7172	Intermediate Similarity	NPD7128	Approved
0.7172	Intermediate Similarity	NPD5739	Approved
0.7128	Intermediate Similarity	NPD5210	Approved
0.7128	Intermediate Similarity	NPD4629	Approved
0.7108	Intermediate Similarity	NPD4190	Phase 3
0.7108	Intermediate Similarity	NPD5275	Approved
0.7093	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD7638	Approved
0.7065	Intermediate Similarity	NPD4096	Approved
0.7053	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5222	Approved
0.7053	Intermediate Similarity	NPD5221	Approved
0.7053	Intermediate Similarity	NPD4697	Phase 3
0.7051	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6899	Approved
0.703	Intermediate Similarity	NPD6881	Approved
0.703	Intermediate Similarity	NPD7320	Approved
0.7024	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6933	Approved
0.7024	Intermediate Similarity	NPD6117	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5360	Phase 3
0.6988	Remote Similarity	NPD4687	Approved
0.6988	Remote Similarity	NPD4058	Approved
0.6979	Remote Similarity	NPD4755	Approved
0.6979	Remote Similarity	NPD7902	Approved
0.6979	Remote Similarity	NPD5959	Approved
0.6979	Remote Similarity	NPD5173	Approved
0.6961	Remote Similarity	NPD6372	Approved
0.6961	Remote Similarity	NPD6373	Approved
0.6951	Remote Similarity	NPD5276	Approved
0.6941	Remote Similarity	NPD6116	Phase 1
0.6931	Remote Similarity	NPD5701	Approved
0.6931	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD3573	Approved
0.6914	Remote Similarity	NPD6922	Approved
0.6914	Remote Similarity	NPD6923	Approved
0.6905	Remote Similarity	NPD3702	Approved
0.6893	Remote Similarity	NPD6883	Approved
0.6893	Remote Similarity	NPD7290	Approved
0.6893	Remote Similarity	NPD7102	Approved
0.6875	Remote Similarity	NPD7614	Phase 1
0.6863	Remote Similarity	NPD6011	Approved
0.686	Remote Similarity	NPD6115	Approved
0.686	Remote Similarity	NPD6118	Approved
0.686	Remote Similarity	NPD6697	Approved
0.686	Remote Similarity	NPD6114	Approved
0.6854	Remote Similarity	NPD5362	Discontinued
0.6848	Remote Similarity	NPD4518	Approved
0.6837	Remote Similarity	NPD4696	Approved
0.6837	Remote Similarity	NPD5286	Approved
0.6837	Remote Similarity	NPD5285	Approved
0.6837	Remote Similarity	NPD4700	Approved
0.6829	Remote Similarity	NPD7143	Approved
0.6829	Remote Similarity	NPD4789	Approved
0.6829	Remote Similarity	NPD7144	Approved
0.6827	Remote Similarity	NPD8130	Phase 1
0.6827	Remote Similarity	NPD6617	Approved
0.6827	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6869	Approved
0.6827	Remote Similarity	NPD6650	Approved
0.6827	Remote Similarity	NPD6649	Approved
0.6827	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD857	Phase 3
0.6809	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD6052	Approved
0.6796	Remote Similarity	NPD6012	Approved
0.6796	Remote Similarity	NPD6014	Approved
0.6796	Remote Similarity	NPD6013	Approved
0.6782	Remote Similarity	NPD6929	Approved
0.6774	Remote Similarity	NPD6051	Approved
0.6771	Remote Similarity	NPD5654	Approved
0.6768	Remote Similarity	NPD5223	Approved
0.6762	Remote Similarity	NPD8297	Approved
0.6762	Remote Similarity	NPD6882	Approved
0.6747	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7152	Approved
0.6747	Remote Similarity	NPD7151	Approved
0.6747	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7150	Approved
0.6705	Remote Similarity	NPD5368	Approved
0.6705	Remote Similarity	NPD6930	Phase 2
0.6705	Remote Similarity	NPD6931	Approved
0.67	Remote Similarity	NPD5091	Approved
0.67	Remote Similarity	NPD5225	Approved
0.67	Remote Similarity	NPD5226	Approved
0.67	Remote Similarity	NPD5224	Approved
0.67	Remote Similarity	NPD4633	Approved
0.67	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6634	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5175	Approved
0.6634	Remote Similarity	NPD4754	Approved
0.6632	Remote Similarity	NPD6411	Approved
0.6629	Remote Similarity	NPD5369	Approved
0.6629	Remote Similarity	NPD6902	Approved
0.6627	Remote Similarity	NPD4245	Approved
0.6627	Remote Similarity	NPD4244	Approved
0.6622	Remote Similarity	NPD4266	Approved
0.6622	Remote Similarity	NPD3196	Approved
0.6622	Remote Similarity	NPD3195	Phase 2
0.6622	Remote Similarity	NPD3194	Approved
0.6602	Remote Similarity	NPD6412	Phase 2
0.6602	Remote Similarity	NPD6614	Approved
0.6574	Remote Similarity	NPD6868	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