NPASS Compound

Structure

NPC48362 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 2.5981 3.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 3.8660 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 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 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 5.4641 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 20 1 1 0 0 0 15 18 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 22 1 1 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	3.308
LogD:	3.522
LogS:	-3.812
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	4.471
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	2.647292785695754e-05
Pgp-inhibitor:	0.54
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.638
Plasma Protein Binding (PPB):	84.82909393310547%
Volume Distribution (VD):	0.839
Pgp-substrate:	6.720644950866699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.318
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.202
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	5.123
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.702
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.203
Carcinogencity:	0.044
Eye Corrosion:	0.096
Eye Irritation:	0.883
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC48362

Natural Product ID:	NPC48362
*Common Name:**	Lonchophylloid B
IUPAC Name:	1-[(2R,4aS,4bR,7S,8aR)-7-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]-2-hydroxyethanone
Synonyms:
Standard InCHIKey:	QPLUSCGQBUSKOF-WKKSIBQESA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-18(2)15-6-5-13-11-19(3,17(23)12-21)9-7-14(13)20(15,4)10-8-16(18)22/h11,14-16,21-22H,5-10,12H2,1-4H3/t14-,15-,16-,19+,20+/m0/s1
SMILES:	CC1(C)[C@@H]2CCC3=C[C@@](C)(CC[C@@H]3[C@@]2(C)CC[C@@H]1O)C(=O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511202
PubChem CID:	643002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10514302]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9461658]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	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
ED50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	ED50	=	195.0	uM	PMID[512934]

☑ 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 NPC48362 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	176
0.1-0.2	1186
0.2-0.3	4970
0.3-0.4	14411
0.4-0.5	9448
0.5-0.6	5889
0.6-0.7	4338
0.7-0.8	1889
0.8-0.85	324
0.85-0.9	60
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC470574
0.9136	High Similarity	NPC133954
0.9024	High Similarity	NPC475862
0.9024	High Similarity	NPC74363
0.9024	High Similarity	NPC51014
0.9024	High Similarity	NPC213412
0.8941	High Similarity	NPC474525
0.8929	High Similarity	NPC474245
0.8916	High Similarity	NPC73064
0.8875	High Similarity	NPC14151
0.8824	High Similarity	NPC46441
0.881	High Similarity	NPC472802
0.8795	High Similarity	NPC73038
0.8795	High Similarity	NPC158393
0.8795	High Similarity	NPC477579
0.8795	High Similarity	NPC325594
0.8795	High Similarity	NPC472986
0.8795	High Similarity	NPC94666
0.8795	High Similarity	NPC235341
0.8795	High Similarity	NPC472985
0.8795	High Similarity	NPC95594
0.8795	High Similarity	NPC20688
0.878	High Similarity	NPC59453
0.878	High Similarity	NPC180834
0.878	High Similarity	NPC221758
0.8765	High Similarity	NPC151519
0.8765	High Similarity	NPC212083
0.875	High Similarity	NPC2482
0.8736	High Similarity	NPC23170
0.8736	High Similarity	NPC245972
0.8736	High Similarity	NPC196485
0.8721	High Similarity	NPC185936
0.8721	High Similarity	NPC168027
0.8706	High Similarity	NPC69627
0.8706	High Similarity	NPC76879
0.8706	High Similarity	NPC472973
0.869	High Similarity	NPC298904
0.869	High Similarity	NPC130577
0.869	High Similarity	NPC142361
0.869	High Similarity	NPC51700
0.869	High Similarity	NPC88716
0.869	High Similarity	NPC474684
0.869	High Similarity	NPC102683
0.869	High Similarity	NPC68160
0.869	High Similarity	NPC142415
0.869	High Similarity	NPC293564
0.869	High Similarity	NPC18064
0.869	High Similarity	NPC171203
0.869	High Similarity	NPC475740
0.869	High Similarity	NPC307426
0.869	High Similarity	NPC98442
0.869	High Similarity	NPC242468
0.8642	High Similarity	NPC473420
0.8642	High Similarity	NPC328264
0.8642	High Similarity	NPC3915
0.8621	High Similarity	NPC12722
0.8608	High Similarity	NPC472746
0.8608	High Similarity	NPC197659
0.8605	High Similarity	NPC85173
0.8605	High Similarity	NPC291028
0.8588	High Similarity	NPC193360
0.8588	High Similarity	NPC17733
0.8588	High Similarity	NPC181225
0.8588	High Similarity	NPC246708
0.8588	High Similarity	NPC470629
0.8588	High Similarity	NPC290690
0.8588	High Similarity	NPC230387
0.8588	High Similarity	NPC182797
0.8588	High Similarity	NPC158778
0.8588	High Similarity	NPC473242
0.8588	High Similarity	NPC52169
0.8588	High Similarity	NPC471722
0.8588	High Similarity	NPC474512
0.8588	High Similarity	NPC206060
0.8588	High Similarity	NPC328539
0.8588	High Similarity	NPC40552
0.8571	High Similarity	NPC94755
0.8571	High Similarity	NPC474732
0.8571	High Similarity	NPC145879
0.8571	High Similarity	NPC72133
0.8571	High Similarity	NPC31564
0.8571	High Similarity	NPC474733
0.8571	High Similarity	NPC474778
0.8571	High Similarity	NPC470955
0.8571	High Similarity	NPC327115
0.8571	High Similarity	NPC72638
0.8554	High Similarity	NPC214043
0.8554	High Similarity	NPC237712
0.8554	High Similarity	NPC82902
0.8554	High Similarity	NPC85774
0.8539	High Similarity	NPC157113
0.8539	High Similarity	NPC62516
0.8537	High Similarity	NPC103486
0.8537	High Similarity	NPC163236
0.8537	High Similarity	NPC310989
0.8523	High Similarity	NPC474328
0.8519	High Similarity	NPC104120
0.8519	High Similarity	NPC148685
0.8519	High Similarity	NPC157895
0.8506	High Similarity	NPC86266
0.8506	High Similarity	NPC212301
0.8506	High Similarity	NPC158030
0.8506	High Similarity	NPC110657
0.8506	High Similarity	NPC65120
0.8506	High Similarity	NPC145067
0.8506	High Similarity	NPC272746
0.8506	High Similarity	NPC472978
0.8506	High Similarity	NPC472975
0.8506	High Similarity	NPC4036
0.8506	High Similarity	NPC105189
0.8506	High Similarity	NPC233455
0.8488	Intermediate Similarity	NPC225585
0.8488	Intermediate Similarity	NPC130520
0.8488	Intermediate Similarity	NPC59263
0.8488	Intermediate Similarity	NPC25906
0.8488	Intermediate Similarity	NPC293048
0.8488	Intermediate Similarity	NPC198664
0.8488	Intermediate Similarity	NPC1015
0.8488	Intermediate Similarity	NPC270768
0.8488	Intermediate Similarity	NPC119416
0.8488	Intermediate Similarity	NPC275740
0.8488	Intermediate Similarity	NPC86319
0.8488	Intermediate Similarity	NPC127689
0.8488	Intermediate Similarity	NPC309603
0.8488	Intermediate Similarity	NPC234346
0.8488	Intermediate Similarity	NPC161751
0.8488	Intermediate Similarity	NPC143232
0.8488	Intermediate Similarity	NPC274330
0.8488	Intermediate Similarity	NPC475921
0.8488	Intermediate Similarity	NPC121798
0.8488	Intermediate Similarity	NPC32830
0.8488	Intermediate Similarity	NPC31985
0.8488	Intermediate Similarity	NPC263393
0.8488	Intermediate Similarity	NPC470588
0.8488	Intermediate Similarity	NPC290972
0.8488	Intermediate Similarity	NPC474704
0.8488	Intermediate Similarity	NPC474972
0.8488	Intermediate Similarity	NPC473999
0.8488	Intermediate Similarity	NPC61543
0.8488	Intermediate Similarity	NPC95246
0.8488	Intermediate Similarity	NPC64872
0.8481	Intermediate Similarity	NPC1973
0.8481	Intermediate Similarity	NPC167873
0.8471	Intermediate Similarity	NPC71507
0.8471	Intermediate Similarity	NPC477926
0.8471	Intermediate Similarity	NPC159046
0.8471	Intermediate Similarity	NPC233836
0.8471	Intermediate Similarity	NPC58063
0.8471	Intermediate Similarity	NPC141292
0.8471	Intermediate Similarity	NPC187376
0.8462	Intermediate Similarity	NPC477138
0.8462	Intermediate Similarity	NPC243342
0.8462	Intermediate Similarity	NPC91858
0.8452	Intermediate Similarity	NPC274724
0.8452	Intermediate Similarity	NPC197823
0.8452	Intermediate Similarity	NPC474218
0.8452	Intermediate Similarity	NPC471224
0.8434	Intermediate Similarity	NPC64600
0.8434	Intermediate Similarity	NPC105173
0.8427	Intermediate Similarity	NPC280725
0.8427	Intermediate Similarity	NPC272617
0.8415	Intermediate Similarity	NPC473217
0.8415	Intermediate Similarity	NPC121984
0.8409	Intermediate Similarity	NPC211230
0.8409	Intermediate Similarity	NPC475255
0.8409	Intermediate Similarity	NPC170220
0.8409	Intermediate Similarity	NPC214756
0.8409	Intermediate Similarity	NPC141497
0.8409	Intermediate Similarity	NPC107674
0.8409	Intermediate Similarity	NPC295643
0.8409	Intermediate Similarity	NPC272075
0.8395	Intermediate Similarity	NPC474113
0.8395	Intermediate Similarity	NPC308038
0.8391	Intermediate Similarity	NPC191684
0.8391	Intermediate Similarity	NPC126369
0.8391	Intermediate Similarity	NPC193750
0.8391	Intermediate Similarity	NPC290614
0.8391	Intermediate Similarity	NPC470589
0.8391	Intermediate Similarity	NPC111110
0.8391	Intermediate Similarity	NPC86372
0.8391	Intermediate Similarity	NPC210037
0.8391	Intermediate Similarity	NPC273621
0.8391	Intermediate Similarity	NPC477872
0.8391	Intermediate Similarity	NPC172361
0.8391	Intermediate Similarity	NPC7260
0.8391	Intermediate Similarity	NPC18872
0.8391	Intermediate Similarity	NPC120968
0.8391	Intermediate Similarity	NPC48010
0.8391	Intermediate Similarity	NPC126993
0.8391	Intermediate Similarity	NPC227467
0.8391	Intermediate Similarity	NPC130278
0.8375	Intermediate Similarity	NPC325946
0.8375	Intermediate Similarity	NPC74995
0.8372	Intermediate Similarity	NPC474925
0.8372	Intermediate Similarity	NPC143767
0.8372	Intermediate Similarity	NPC328313
0.8372	Intermediate Similarity	NPC292491
0.8372	Intermediate Similarity	NPC53911
0.8372	Intermediate Similarity	NPC471724
0.8372	Intermediate Similarity	NPC310752

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 NPC48362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1565
0.2-0.3	3954
0.3-0.4	2355
0.4-0.5	666
0.5-0.6	162
0.6-0.7	149
0.7-0.8	113
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8795	High Similarity	NPD3618	Phase 1
0.878	High Similarity	NPD4786	Approved
0.8765	High Similarity	NPD3667	Approved
0.8706	High Similarity	NPD5328	Approved
0.8506	High Similarity	NPD7515	Phase 2
0.8506	High Similarity	NPD6079	Approved
0.8353	Intermediate Similarity	NPD5279	Phase 3
0.8333	Intermediate Similarity	NPD3665	Phase 1
0.8333	Intermediate Similarity	NPD4697	Phase 3
0.8333	Intermediate Similarity	NPD3133	Approved
0.8333	Intermediate Similarity	NPD5221	Approved
0.8333	Intermediate Similarity	NPD3666	Approved
0.8333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5222	Approved
0.8293	Intermediate Similarity	NPD4695	Discontinued
0.8242	Intermediate Similarity	NPD5173	Approved
0.8242	Intermediate Similarity	NPD4755	Approved
0.8202	Intermediate Similarity	NPD4202	Approved
0.8111	Intermediate Similarity	NPD7748	Approved
0.8068	Intermediate Similarity	NPD4753	Phase 2
0.8065	Intermediate Similarity	NPD4700	Approved
0.8065	Intermediate Similarity	NPD4696	Approved
0.8065	Intermediate Similarity	NPD5285	Approved
0.8065	Intermediate Similarity	NPD5286	Approved
0.8023	Intermediate Similarity	NPD5329	Approved
0.7979	Intermediate Similarity	NPD5223	Approved
0.7952	Intermediate Similarity	NPD7645	Phase 2
0.7907	Intermediate Similarity	NPD3668	Phase 3
0.7907	Intermediate Similarity	NPD4197	Approved
0.7895	Intermediate Similarity	NPD4633	Approved
0.7895	Intermediate Similarity	NPD5226	Approved
0.7895	Intermediate Similarity	NPD5225	Approved
0.7895	Intermediate Similarity	NPD5224	Approved
0.7895	Intermediate Similarity	NPD5211	Phase 2
0.7849	Intermediate Similarity	NPD7902	Approved
0.7835	Intermediate Similarity	NPD5739	Approved
0.7835	Intermediate Similarity	NPD6675	Approved
0.7835	Intermediate Similarity	NPD6402	Approved
0.7835	Intermediate Similarity	NPD7128	Approved
0.7831	Intermediate Similarity	NPD3617	Approved
0.7816	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5175	Approved
0.7812	Intermediate Similarity	NPD5174	Approved
0.7812	Intermediate Similarity	NPD4754	Approved
0.7802	Intermediate Similarity	NPD6399	Phase 3
0.7732	Intermediate Similarity	NPD5141	Approved
0.7683	Intermediate Similarity	NPD6942	Approved
0.7683	Intermediate Similarity	NPD7339	Approved
0.7677	Intermediate Similarity	NPD6881	Approved
0.7677	Intermediate Similarity	NPD7320	Approved
0.7677	Intermediate Similarity	NPD6899	Approved
0.7674	Intermediate Similarity	NPD4223	Phase 3
0.7674	Intermediate Similarity	NPD4221	Approved
0.766	Intermediate Similarity	NPD6084	Phase 2
0.766	Intermediate Similarity	NPD6083	Phase 2
0.7653	Intermediate Similarity	NPD4768	Approved
0.7653	Intermediate Similarity	NPD4767	Approved
0.7647	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7525	Registered
0.7634	Intermediate Similarity	NPD5210	Approved
0.7634	Intermediate Similarity	NPD4629	Approved
0.76	Intermediate Similarity	NPD6373	Approved
0.76	Intermediate Similarity	NPD6372	Approved
0.759	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5701	Approved
0.7576	Intermediate Similarity	NPD5697	Approved
0.7556	Intermediate Similarity	NPD6672	Approved
0.7556	Intermediate Similarity	NPD5737	Approved
0.7528	Intermediate Similarity	NPD4694	Approved
0.7528	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD5690	Phase 2
0.7528	Intermediate Similarity	NPD7334	Approved
0.7528	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD7521	Approved
0.7528	Intermediate Similarity	NPD6409	Approved
0.7528	Intermediate Similarity	NPD7146	Approved
0.7528	Intermediate Similarity	NPD5280	Approved
0.7527	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7900	Approved
0.7525	Intermediate Similarity	NPD7290	Approved
0.7525	Intermediate Similarity	NPD7102	Approved
0.7525	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD4730	Approved
0.75	Intermediate Similarity	NPD5168	Approved
0.75	Intermediate Similarity	NPD5128	Approved
0.75	Intermediate Similarity	NPD4729	Approved
0.7473	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD8130	Phase 1
0.7451	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6617	Approved
0.7451	Intermediate Similarity	NPD6650	Approved
0.7451	Intermediate Similarity	NPD6869	Approved
0.7451	Intermediate Similarity	NPD6649	Approved
0.7451	Intermediate Similarity	NPD6847	Approved
0.7426	Intermediate Similarity	NPD6012	Approved
0.7426	Intermediate Similarity	NPD6014	Approved
0.7426	Intermediate Similarity	NPD6013	Approved
0.7386	Intermediate Similarity	NPD4788	Approved
0.7379	Intermediate Similarity	NPD6882	Approved
0.7379	Intermediate Similarity	NPD8297	Approved
0.7363	Intermediate Similarity	NPD6903	Approved
0.7363	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5250	Approved
0.7353	Intermediate Similarity	NPD5251	Approved
0.7353	Intermediate Similarity	NPD4634	Approved
0.7353	Intermediate Similarity	NPD5249	Phase 3
0.7353	Intermediate Similarity	NPD5248	Approved
0.7353	Intermediate Similarity	NPD5247	Approved
0.7353	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5135	Approved
0.7353	Intermediate Similarity	NPD5169	Approved
0.7333	Intermediate Similarity	NPD4519	Discontinued
0.7333	Intermediate Similarity	NPD4693	Phase 3
0.7333	Intermediate Similarity	NPD6098	Approved
0.7333	Intermediate Similarity	NPD4138	Approved
0.7333	Intermediate Similarity	NPD5205	Approved
0.7333	Intermediate Similarity	NPD4690	Approved
0.7333	Intermediate Similarity	NPD4688	Approved
0.7333	Intermediate Similarity	NPD4689	Approved
0.7333	Intermediate Similarity	NPD4623	Approved
0.7317	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6411	Approved
0.7284	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5216	Approved
0.7282	Intermediate Similarity	NPD5215	Approved
0.7282	Intermediate Similarity	NPD5127	Approved
0.7282	Intermediate Similarity	NPD5217	Approved
0.7263	Intermediate Similarity	NPD5695	Phase 3
0.7253	Intermediate Similarity	NPD3573	Approved
0.7216	Intermediate Similarity	NPD7638	Approved
0.7216	Intermediate Similarity	NPD5696	Approved
0.7195	Intermediate Similarity	NPD4789	Approved
0.717	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD6926	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7097	Intermediate Similarity	NPD6101	Approved
0.7097	Intermediate Similarity	NPD6904	Approved
0.7097	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6080	Approved
0.7097	Intermediate Similarity	NPD6673	Approved
0.7075	Intermediate Similarity	NPD5167	Approved
0.7073	Intermediate Similarity	NPD4137	Phase 3
0.7059	Intermediate Similarity	NPD3703	Phase 2
0.7059	Intermediate Similarity	NPD8264	Approved
0.7037	Intermediate Similarity	NPD6335	Approved
0.7009	Intermediate Similarity	NPD6274	Approved
0.6988	Remote Similarity	NPD4245	Approved
0.6988	Remote Similarity	NPD4244	Approved
0.6988	Remote Similarity	NPD4691	Approved
0.6988	Remote Similarity	NPD4747	Approved
0.6977	Remote Similarity	NPD6117	Approved
0.6977	Remote Similarity	NPD6933	Approved
0.6972	Remote Similarity	NPD7100	Approved
0.6972	Remote Similarity	NPD7101	Approved
0.6966	Remote Similarity	NPD4692	Approved
0.6966	Remote Similarity	NPD4139	Approved
0.6951	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6009	Approved
0.6944	Remote Similarity	NPD6317	Approved
0.6941	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4195	Approved
0.6914	Remote Similarity	NPD7331	Phase 2
0.6909	Remote Similarity	NPD6054	Approved
0.6909	Remote Similarity	NPD6059	Approved
0.6907	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7150	Approved
0.6905	Remote Similarity	NPD7152	Approved
0.6905	Remote Similarity	NPD7151	Approved
0.6905	Remote Similarity	NPD4243	Approved
0.6897	Remote Similarity	NPD6116	Phase 1
0.6893	Remote Similarity	NPD6412	Phase 2
0.6881	Remote Similarity	NPD6313	Approved
0.6881	Remote Similarity	NPD6314	Approved
0.6875	Remote Similarity	NPD5133	Approved
0.6869	Remote Similarity	NPD5290	Discontinued
0.6867	Remote Similarity	NPD3698	Phase 2
0.6867	Remote Similarity	NPD6923	Approved
0.6867	Remote Similarity	NPD6922	Approved
0.6854	Remote Similarity	NPD7509	Discontinued
0.6848	Remote Similarity	NPD1696	Phase 3
0.6847	Remote Similarity	NPD6909	Approved
0.6847	Remote Similarity	NPD6908	Approved
0.6842	Remote Similarity	NPD4096	Approved
0.6818	Remote Similarity	NPD6118	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6114	Approved
0.6818	Remote Similarity	NPD6115	Approved
0.6818	Remote Similarity	NPD6697	Approved
0.679	Remote Similarity	NPD7341	Phase 2
0.679	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7115	Discovery

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