NPASS Compound

Structure

NPC52108 OpenBabel07101718192D 25 27 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 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 -4.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 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 -1.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 -0.8660 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 0.8660 1.5000 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 -0.8660 1.5000 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 -1.7321 -0.0000 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 -4.7321 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 13 25 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 18 22 1 6 0 0 0 19 20 1 0 0 0 0 19 24 1 6 0 0 0 20 21 1 6 0 0 0 20 22 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	266.85
Volume:	145.715
LogP:	2.274
LogD:	1.296
LogS:	-2.598
# Rotatable Bonds:	1
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.821
Synthetic Accessibility Score:	2.833
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.665
MDCK Permeability:	1.726774098642636e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.304
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.247

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.302
Plasma Protein Binding (PPB):	92.2219009399414%
Volume Distribution (VD):	0.308
Pgp-substrate:	18.98087501525879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	1.153
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.166
Carcinogencity:	0.853
Eye Corrosion:	0.05
Eye Irritation:	0.986
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC52108

Natural Product ID:	NPC52108
*Common Name:**	6Beta-Hydroxy-18-Acetoxycassan-13,15-Diene
IUPAC Name:	[(1R,4aR,4bS,8aR,10R,10aR)-7-ethenyl-10-hydroxy-1,4a,8-trimethyl-2,3,4,4b,5,6,8a,9,10,10a-decahydrophenanthren-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	SVXPDLNSXIXYEA-KINXCBNHSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-6-16-8-9-18-17(14(16)2)12-19(24)20-21(4,13-25-15(3)23)10-7-11-22(18,20)5/h6,17-20,24H,1,7-13H2,2-5H3/t17-,18-,19+,20-,21-,22+/m0/s1
SMILES:	C=CC1=C(C)[C@@H]2C[C@H]([C@H]3[C@@](C)(CCC[C@]3(C)[C@H]2CC1)COC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514444
PubChem CID:	21674168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane diterpenoids

*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
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880308]
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497945]
NPO10318	Myrospermum frutescens	Species	Fabaceae	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	4
Others	1

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT859	Cell Line	HFF	Homo sapiens	IC50	=	118000.0	nM	PMID[493740]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	11000.0	nM	PMID[493739]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	11500.0	nM	PMID[493740]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	25900.0	nM	PMID[493740]
NPT2	Others	Unspecified		Ratio IC50	=	8.0	n.a.	PMID[493740]

☑ 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 NPC52108 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	177
0.1-0.2	1053
0.2-0.3	4504
0.3-0.4	13584
0.4-0.5	10470
0.5-0.6	6249
0.6-0.7	4766
0.7-0.8	1791
0.8-0.85	88
0.85-0.9	8
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474789
0.9359	High Similarity	NPC269791
0.9277	High Similarity	NPC16265
0.9241	High Similarity	NPC142163
0.9091	High Similarity	NPC106432
0.8987	High Similarity	NPC100906
0.8916	High Similarity	NPC84121
0.8916	High Similarity	NPC137306
0.8795	High Similarity	NPC191965
0.869	High Similarity	NPC325594
0.869	High Similarity	NPC474970
0.8571	High Similarity	NPC109528
0.85	High Similarity	NPC283619
0.8481	Intermediate Similarity	NPC291503
0.8471	Intermediate Similarity	NPC73038
0.8462	Intermediate Similarity	NPC182717
0.8462	Intermediate Similarity	NPC68443
0.8427	Intermediate Similarity	NPC215700
0.8409	Intermediate Similarity	NPC301244
0.8395	Intermediate Similarity	NPC72507
0.8391	Intermediate Similarity	NPC161751
0.8391	Intermediate Similarity	NPC95246
0.8391	Intermediate Similarity	NPC474972
0.8391	Intermediate Similarity	NPC473647
0.8354	Intermediate Similarity	NPC91858
0.8354	Intermediate Similarity	NPC477138
0.8354	Intermediate Similarity	NPC243342
0.8353	Intermediate Similarity	NPC164424
0.8333	Intermediate Similarity	NPC312480
0.8333	Intermediate Similarity	NPC110799
0.8313	Intermediate Similarity	NPC290495
0.8313	Intermediate Similarity	NPC195334
0.8295	Intermediate Similarity	NPC280149
0.8295	Intermediate Similarity	NPC221111
0.8276	Intermediate Similarity	NPC40552
0.8276	Intermediate Similarity	NPC246708
0.8272	Intermediate Similarity	NPC471798
0.8256	Intermediate Similarity	NPC72638
0.8235	Intermediate Similarity	NPC102048
0.8228	Intermediate Similarity	NPC471799
0.8222	Intermediate Similarity	NPC80365
0.8214	Intermediate Similarity	NPC73882
0.8214	Intermediate Similarity	NPC256112
0.8214	Intermediate Similarity	NPC286786
0.8214	Intermediate Similarity	NPC15910
0.8202	Intermediate Similarity	NPC477574
0.8193	Intermediate Similarity	NPC281880
0.8182	Intermediate Similarity	NPC84271
0.8182	Intermediate Similarity	NPC102414
0.8182	Intermediate Similarity	NPC30522
0.8182	Intermediate Similarity	NPC77168
0.8182	Intermediate Similarity	NPC470588
0.8182	Intermediate Similarity	NPC25906
0.8182	Intermediate Similarity	NPC290972
0.8182	Intermediate Similarity	NPC474686
0.8182	Intermediate Similarity	NPC64872
0.8182	Intermediate Similarity	NPC32055
0.8171	Intermediate Similarity	NPC300499
0.8161	Intermediate Similarity	NPC293564
0.8161	Intermediate Similarity	NPC171203
0.8161	Intermediate Similarity	NPC142361
0.8161	Intermediate Similarity	NPC307426
0.8161	Intermediate Similarity	NPC68160
0.8161	Intermediate Similarity	NPC242468
0.8161	Intermediate Similarity	NPC130577
0.8161	Intermediate Similarity	NPC142415
0.8161	Intermediate Similarity	NPC88716
0.8161	Intermediate Similarity	NPC51700
0.8161	Intermediate Similarity	NPC98442
0.8161	Intermediate Similarity	NPC102683
0.8161	Intermediate Similarity	NPC474684
0.8161	Intermediate Similarity	NPC18064
0.8161	Intermediate Similarity	NPC245004
0.814	Intermediate Similarity	NPC476602
0.814	Intermediate Similarity	NPC76333
0.8125	Intermediate Similarity	NPC471797
0.8125	Intermediate Similarity	NPC100334
0.8125	Intermediate Similarity	NPC71152
0.8118	Intermediate Similarity	NPC57370
0.8118	Intermediate Similarity	NPC237795
0.8118	Intermediate Similarity	NPC132386
0.8118	Intermediate Similarity	NPC82538
0.8118	Intermediate Similarity	NPC476927
0.8118	Intermediate Similarity	NPC473592
0.8111	Intermediate Similarity	NPC63118
0.8111	Intermediate Similarity	NPC470224
0.8111	Intermediate Similarity	NPC49776
0.8111	Intermediate Similarity	NPC474436
0.8111	Intermediate Similarity	NPC86368
0.8101	Intermediate Similarity	NPC167706
0.8101	Intermediate Similarity	NPC242001
0.8095	Intermediate Similarity	NPC473420
0.8095	Intermediate Similarity	NPC108476
0.8095	Intermediate Similarity	NPC159148
0.8095	Intermediate Similarity	NPC476646
0.8095	Intermediate Similarity	NPC116202
0.8095	Intermediate Similarity	NPC474955
0.8095	Intermediate Similarity	NPC170303
0.809	Intermediate Similarity	NPC477872
0.809	Intermediate Similarity	NPC210037
0.809	Intermediate Similarity	NPC474728
0.809	Intermediate Similarity	NPC471896
0.809	Intermediate Similarity	NPC290614
0.809	Intermediate Similarity	NPC273621
0.809	Intermediate Similarity	NPC113989
0.809	Intermediate Similarity	NPC227467
0.809	Intermediate Similarity	NPC18872
0.809	Intermediate Similarity	NPC120968
0.809	Intermediate Similarity	NPC120840
0.809	Intermediate Similarity	NPC310479
0.809	Intermediate Similarity	NPC130278
0.809	Intermediate Similarity	NPC7260
0.8072	Intermediate Similarity	NPC44083
0.8072	Intermediate Similarity	NPC153987
0.8072	Intermediate Similarity	NPC242767
0.8068	Intermediate Similarity	NPC470629
0.8068	Intermediate Similarity	NPC181225
0.8068	Intermediate Similarity	NPC290690
0.8068	Intermediate Similarity	NPC182797
0.8068	Intermediate Similarity	NPC52169
0.8068	Intermediate Similarity	NPC474512
0.8068	Intermediate Similarity	NPC17733
0.8068	Intermediate Similarity	NPC24816
0.8068	Intermediate Similarity	NPC473242
0.8065	Intermediate Similarity	NPC477813
0.8049	Intermediate Similarity	NPC40394
0.8049	Intermediate Similarity	NPC472805
0.8049	Intermediate Similarity	NPC101475
0.8049	Intermediate Similarity	NPC91594
0.8049	Intermediate Similarity	NPC130136
0.8049	Intermediate Similarity	NPC90979
0.8049	Intermediate Similarity	NPC34177
0.8049	Intermediate Similarity	NPC157996
0.8046	Intermediate Similarity	NPC6979
0.8046	Intermediate Similarity	NPC82979
0.8043	Intermediate Similarity	NPC327179
0.8043	Intermediate Similarity	NPC304899
0.8043	Intermediate Similarity	NPC88847
0.8043	Intermediate Similarity	NPC253115
0.8043	Intermediate Similarity	NPC88009
0.8025	Intermediate Similarity	NPC477923
0.8025	Intermediate Similarity	NPC66566
0.8025	Intermediate Similarity	NPC34700
0.8025	Intermediate Similarity	NPC138374
0.8023	Intermediate Similarity	NPC302360
0.8023	Intermediate Similarity	NPC306951
0.8023	Intermediate Similarity	NPC171789
0.8022	Intermediate Similarity	NPC49670
0.8022	Intermediate Similarity	NPC211238
0.8	Intermediate Similarity	NPC474979
0.8	Intermediate Similarity	NPC285184
0.8	Intermediate Similarity	NPC470571
0.8	Intermediate Similarity	NPC187722
0.8	Intermediate Similarity	NPC212948
0.8	Intermediate Similarity	NPC2524
0.8	Intermediate Similarity	NPC60755
0.8	Intermediate Similarity	NPC77099
0.8	Intermediate Similarity	NPC470590
0.8	Intermediate Similarity	NPC20853
0.8	Intermediate Similarity	NPC472504
0.8	Intermediate Similarity	NPC105189
0.7979	Intermediate Similarity	NPC254567
0.7979	Intermediate Similarity	NPC474571
0.7978	Intermediate Similarity	NPC262858
0.7978	Intermediate Similarity	NPC225585
0.7978	Intermediate Similarity	NPC263393
0.7978	Intermediate Similarity	NPC234346
0.7978	Intermediate Similarity	NPC475921
0.7978	Intermediate Similarity	NPC130520
0.7978	Intermediate Similarity	NPC121798
0.7978	Intermediate Similarity	NPC274330
0.7978	Intermediate Similarity	NPC474704
0.7978	Intermediate Similarity	NPC475049
0.7978	Intermediate Similarity	NPC143232
0.7978	Intermediate Similarity	NPC472240
0.7978	Intermediate Similarity	NPC293048
0.7978	Intermediate Similarity	NPC59263
0.7978	Intermediate Similarity	NPC20946
0.7978	Intermediate Similarity	NPC61543
0.7978	Intermediate Similarity	NPC270768
0.7978	Intermediate Similarity	NPC198664
0.7978	Intermediate Similarity	NPC127689
0.7976	Intermediate Similarity	NPC206735
0.7976	Intermediate Similarity	NPC96362
0.7976	Intermediate Similarity	NPC287749
0.7975	Intermediate Similarity	NPC145498
0.7975	Intermediate Similarity	NPC92801
0.7957	Intermediate Similarity	NPC210337
0.7957	Intermediate Similarity	NPC141401
0.7957	Intermediate Similarity	NPC99726
0.7957	Intermediate Similarity	NPC475032
0.7957	Intermediate Similarity	NPC21728
0.7957	Intermediate Similarity	NPC475033
0.7955	Intermediate Similarity	NPC71507
0.7955	Intermediate Similarity	NPC233836
0.7955	Intermediate Similarity	NPC478104
0.7955	Intermediate Similarity	NPC159046
0.7955	Intermediate Similarity	NPC477926
0.7955	Intermediate Similarity	NPC166857
0.7955	Intermediate Similarity	NPC187376

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 NPC52108 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1290
0.2-0.3	3853
0.3-0.4	2569
0.4-0.5	811
0.5-0.6	207
0.6-0.7	200
0.7-0.8	61
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD7645	Phase 2
0.7826	Intermediate Similarity	NPD7748	Approved
0.7802	Intermediate Similarity	NPD7515	Phase 2
0.7766	Intermediate Similarity	NPD7902	Approved
0.7765	Intermediate Similarity	NPD7525	Registered
0.7717	Intermediate Similarity	NPD6399	Phase 3
0.7609	Intermediate Similarity	NPD6411	Approved
0.759	Intermediate Similarity	NPD6942	Approved
0.759	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7638	Approved
0.7447	Intermediate Similarity	NPD7900	Approved
0.7447	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3618	Phase 1
0.7426	Intermediate Similarity	NPD6899	Approved
0.7426	Intermediate Similarity	NPD6881	Approved
0.7423	Intermediate Similarity	NPD7640	Approved
0.7423	Intermediate Similarity	NPD7639	Approved
0.7419	Intermediate Similarity	NPD6079	Approved
0.7416	Intermediate Similarity	NPD4786	Approved
0.74	Intermediate Similarity	NPD7128	Approved
0.74	Intermediate Similarity	NPD6675	Approved
0.74	Intermediate Similarity	NPD5739	Approved
0.74	Intermediate Similarity	NPD6402	Approved
0.7391	Intermediate Similarity	NPD6101	Approved
0.7391	Intermediate Similarity	NPD5328	Approved
0.7391	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3667	Approved
0.7381	Intermediate Similarity	NPD8264	Approved
0.7333	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD7102	Approved
0.7282	Intermediate Similarity	NPD6883	Approved
0.7282	Intermediate Similarity	NPD7290	Approved
0.7262	Intermediate Similarity	NPD6926	Approved
0.7262	Intermediate Similarity	NPD6924	Approved
0.7255	Intermediate Similarity	NPD7320	Approved
0.7255	Intermediate Similarity	NPD6011	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7229	Intermediate Similarity	NPD7152	Approved
0.7229	Intermediate Similarity	NPD7150	Approved
0.7229	Intermediate Similarity	NPD7151	Approved
0.7212	Intermediate Similarity	NPD6649	Approved
0.7212	Intermediate Similarity	NPD6617	Approved
0.7212	Intermediate Similarity	NPD6869	Approved
0.7212	Intermediate Similarity	NPD8130	Phase 1
0.7212	Intermediate Similarity	NPD6650	Approved
0.7212	Intermediate Similarity	NPD6847	Approved
0.7184	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD6372	Approved
0.7184	Intermediate Similarity	NPD6373	Approved
0.7184	Intermediate Similarity	NPD6014	Approved
0.7184	Intermediate Similarity	NPD6012	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7159	Intermediate Similarity	NPD7509	Discontinued
0.7158	Intermediate Similarity	NPD4202	Approved
0.7157	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7108	Intermediate Similarity	NPD7143	Approved
0.7108	Intermediate Similarity	NPD7144	Approved
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7093	Intermediate Similarity	NPD6933	Approved
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7048	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7033	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3665	Phase 1
0.7033	Intermediate Similarity	NPD3666	Approved
0.7033	Intermediate Similarity	NPD3133	Approved
0.7021	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6051	Approved
0.6988	Remote Similarity	NPD6922	Approved
0.6988	Remote Similarity	NPD6923	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6979	Remote Similarity	NPD5778	Approved
0.697	Remote Similarity	NPD4225	Approved
0.6939	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5222	Approved
0.6939	Remote Similarity	NPD5221	Approved
0.6931	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD6695	Phase 3
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.69	Remote Similarity	NPD5285	Approved
0.69	Remote Similarity	NPD4696	Approved
0.69	Remote Similarity	NPD5286	Approved
0.6882	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD4755	Approved
0.6869	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD4784	Approved
0.686	Remote Similarity	NPD4785	Approved
0.6857	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4195	Approved
0.6854	Remote Similarity	NPD6929	Approved
0.6832	Remote Similarity	NPD5223	Approved
0.6824	Remote Similarity	NPD4243	Approved
0.6818	Remote Similarity	NPD6335	Approved
0.6818	Remote Similarity	NPD6932	Approved
0.6818	Remote Similarity	NPD6116	Phase 1
0.68	Remote Similarity	NPD5290	Discontinued
0.6789	Remote Similarity	NPD6868	Approved
0.6786	Remote Similarity	NPD7503	Approved
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD4748	Discontinued
0.6778	Remote Similarity	NPD6930	Phase 2
0.6774	Remote Similarity	NPD1694	Approved
0.6768	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5225	Approved
0.6765	Remote Similarity	NPD5224	Approved
0.6765	Remote Similarity	NPD4633	Approved
0.6765	Remote Similarity	NPD5211	Phase 2
0.6765	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD4632	Approved
0.6757	Remote Similarity	NPD7100	Approved
0.6757	Remote Similarity	NPD7101	Approved
0.6742	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7145	Approved
0.6733	Remote Similarity	NPD4700	Approved
0.6727	Remote Similarity	NPD6317	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6705	Remote Similarity	NPD6117	Approved
0.6702	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5175	Approved
0.6699	Remote Similarity	NPD5174	Approved
0.6698	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6636	Remote Similarity	NPD6274	Approved
0.6635	Remote Similarity	NPD5141	Approved
0.6634	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD7524	Approved
0.6632	Remote Similarity	NPD7750	Discontinued
0.6632	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6925	Approved
0.6629	Remote Similarity	NPD5776	Phase 2
0.6604	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5207	Approved
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7514	Phase 3
0.6593	Remote Similarity	NPD7332	Phase 2
0.6591	Remote Similarity	NPD8039	Approved
0.6585	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6009	Approved
0.6571	Remote Similarity	NPD6008	Approved
0.6569	Remote Similarity	NPD6648	Approved
0.6556	Remote Similarity	NPD6115	Approved
0.6556	Remote Similarity	NPD6114	Approved
0.6556	Remote Similarity	NPD6697	Approved
0.6556	Remote Similarity	NPD6118	Approved
0.6549	Remote Similarity	NPD6319	Approved
0.6538	Remote Similarity	NPD4754	Approved
0.6531	Remote Similarity	NPD6050	Approved
0.6531	Remote Similarity	NPD5694	Approved
0.6526	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD6902	Approved
0.6518	Remote Similarity	NPD7327	Approved
0.6518	Remote Similarity	NPD7328	Approved
0.6509	Remote Similarity	NPD6412	Phase 2
0.6505	Remote Similarity	NPD5344	Discontinued
0.6495	Remote Similarity	NPD4753	Phase 2
0.6495	Remote Similarity	NPD6080	Approved
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6904	Approved
0.6491	Remote Similarity	NPD5983	Phase 2
0.6491	Remote Similarity	NPD6909	Approved
0.6491	Remote Similarity	NPD6908	Approved
0.6491	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6683	Phase 2
0.6481	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7492	Approved
0.646	Remote Similarity	NPD7516	Approved
0.6452	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4221	Approved
0.6452	Remote Similarity	NPD4223	Phase 3
0.6449	Remote Similarity	NPD4729	Approved
0.6449	Remote Similarity	NPD4730	Approved
0.6449	Remote Similarity	NPD6686	Approved
0.6429	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5692	Phase 3
0.6421	Remote Similarity	NPD5329	Approved
0.6421	Remote Similarity	NPD6893	Approved
0.6415	Remote Similarity	NPD4768	Approved
0.6415	Remote Similarity	NPD4767	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