NPASS Compound

Structure

NPC71507 OpenBabel07101719252D 33 37 0 0 1 0 0 0 0 0999 V2000 -0.9980 -3.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5860 -3.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8598 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8861 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 1 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 5.0594 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 27 1 6 0 0 0 21 26 1 0 0 0 0 21 28 1 0 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	503.115
LogP:	5.789
LogD:	4.381
LogS:	-5.047
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	4.948
Fsp3:	0.833
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:	-5.311
MDCK Permeability:	1.558446092531085e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.23

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	99.27669525146484%
Volume Distribution (VD):	0.935
Pgp-substrate:	2.740528106689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.229
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	2.246
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.403
Carcinogencity:	0.06
Eye Corrosion:	0.029
Eye Irritation:	0.781
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC71507

Natural Product ID:	NPC71507
*Common Name:**	3Alpha-Hydroxyolean-5,12-Dien-27-Oic Acid
IUPAC Name:	(4aR,6aR,6aR,6bR,10R,12aR,14bR)-10-hydroxy-2,2,4a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,10,11,12,13,14b-dodecahydropicene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	JIPGXRGBUPVACU-IBNURMDSSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-25(2)14-15-27(5)16-17-30(24(32)33)19(20(27)18-25)8-9-22-28(6)12-11-23(31)26(3,4)21(28)10-13-29(22,30)7/h8,10,20,22-23,31H,9,11-18H2,1-7H3,(H,32,33)/t20-,22+,23+,27+,28-,29+,30+/m0/s1
SMILES:	O[C@@H]1CC[C@]2(C(=CC[C@@]3([C@@H]2CC=C2[C@]3(CC[C@@]3([C@H]2CC(C)(C)CC3)C)C(=O)O)C)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557099
PubChem CID:	44236362
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
NPO6947	Astilbe chinensis	Species	Saxifragaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19585998]
NPO6947	Astilbe chinensis	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6947	Astilbe chinensis	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6947	Astilbe chinensis	Species	Saxifragaceae	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

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[486754]
NPT788	Cell Line	SNU1	Homo sapiens	IC50	>	10000.0	nM	PMID[486754]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[486754]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[486754]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[486754]

☑ 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 NPC71507 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	198
0.1-0.2	1180
0.2-0.3	4814
0.3-0.4	14734
0.4-0.5	8627
0.5-0.6	5640
0.6-0.7	4845
0.7-0.8	2117
0.8-0.85	243
0.85-0.9	211
0.9-0.95	86
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC17733
0.9639	High Similarity	NPC470629
0.9639	High Similarity	NPC290690
0.9639	High Similarity	NPC474512
0.9639	High Similarity	NPC181225
0.9639	High Similarity	NPC473242
0.9529	High Similarity	NPC301244
0.9524	High Similarity	NPC143232
0.9524	High Similarity	NPC470588
0.9524	High Similarity	NPC198664
0.9524	High Similarity	NPC274330
0.9518	High Similarity	NPC51700
0.9518	High Similarity	NPC130577
0.9518	High Similarity	NPC98442
0.9518	High Similarity	NPC293564
0.9518	High Similarity	NPC88716
0.9518	High Similarity	NPC18064
0.9518	High Similarity	NPC142415
0.9518	High Similarity	NPC242468
0.9518	High Similarity	NPC68160
0.9518	High Similarity	NPC307426
0.9518	High Similarity	NPC102683
0.9518	High Similarity	NPC171203
0.9419	High Similarity	NPC133579
0.9419	High Similarity	NPC474806
0.9412	High Similarity	NPC126369
0.9412	High Similarity	NPC470589
0.9412	High Similarity	NPC111110
0.9405	High Similarity	NPC40552
0.9405	High Similarity	NPC52169
0.9405	High Similarity	NPC246708
0.9405	High Similarity	NPC182797
0.9398	High Similarity	NPC72638
0.939	High Similarity	NPC171789
0.931	High Similarity	NPC80365
0.9302	High Similarity	NPC187722
0.9294	High Similarity	NPC121798
0.9294	High Similarity	NPC64872
0.9294	High Similarity	NPC263393
0.9294	High Similarity	NPC161751
0.9294	High Similarity	NPC270768
0.9294	High Similarity	NPC59263
0.9294	High Similarity	NPC234346
0.9294	High Similarity	NPC474686
0.9294	High Similarity	NPC61543
0.9294	High Similarity	NPC25906
0.9294	High Similarity	NPC474972
0.9294	High Similarity	NPC225585
0.9294	High Similarity	NPC95246
0.9294	High Similarity	NPC127689
0.9294	High Similarity	NPC293048
0.9294	High Similarity	NPC130520
0.9294	High Similarity	NPC290972
0.9205	High Similarity	NPC32118
0.9195	High Similarity	NPC158059
0.9195	High Similarity	NPC118519
0.9195	High Similarity	NPC202728
0.9195	High Similarity	NPC229281
0.9186	High Similarity	NPC210037
0.9186	High Similarity	NPC86372
0.9186	High Similarity	NPC290614
0.9186	High Similarity	NPC291028
0.9186	High Similarity	NPC227467
0.9186	High Similarity	NPC130278
0.9186	High Similarity	NPC474728
0.9186	High Similarity	NPC273621
0.9186	High Similarity	NPC477872
0.9186	High Similarity	NPC172361
0.9186	High Similarity	NPC7260
0.9186	High Similarity	NPC18872
0.9186	High Similarity	NPC120968
0.9167	High Similarity	NPC56588
0.9157	High Similarity	NPC180834
0.9091	High Similarity	NPC159365
0.9091	High Similarity	NPC114159
0.9091	High Similarity	NPC6818
0.9091	High Similarity	NPC209868
0.9091	High Similarity	NPC191412
0.908	High Similarity	NPC4036
0.908	High Similarity	NPC966
0.908	High Similarity	NPC288833
0.908	High Similarity	NPC84319
0.908	High Similarity	NPC470590
0.908	High Similarity	NPC25299
0.908	High Similarity	NPC145067
0.908	High Similarity	NPC105189
0.908	High Similarity	NPC228784
0.908	High Similarity	NPC155120
0.908	High Similarity	NPC52021
0.908	High Similarity	NPC158030
0.908	High Similarity	NPC285184
0.908	High Similarity	NPC300351
0.908	High Similarity	NPC233455
0.908	High Similarity	NPC474525
0.908	High Similarity	NPC306541
0.908	High Similarity	NPC472149
0.908	High Similarity	NPC38754
0.908	High Similarity	NPC324341
0.908	High Similarity	NPC235884
0.908	High Similarity	NPC77099
0.908	High Similarity	NPC71074
0.908	High Similarity	NPC65120
0.908	High Similarity	NPC282616
0.908	High Similarity	NPC60755
0.9059	High Similarity	NPC73064
0.9048	High Similarity	NPC133954
0.9024	High Similarity	NPC473420
0.9	High Similarity	NPC21728
0.8989	High Similarity	NPC96916
0.8989	High Similarity	NPC473240
0.8977	High Similarity	NPC272075
0.8977	High Similarity	NPC307335
0.8977	High Similarity	NPC295643
0.8977	High Similarity	NPC275809
0.8977	High Similarity	NPC474436
0.8977	High Similarity	NPC214756
0.8977	High Similarity	NPC74855
0.8977	High Similarity	NPC49776
0.8977	High Similarity	NPC86368
0.8977	High Similarity	NPC63118
0.8977	High Similarity	NPC298554
0.8977	High Similarity	NPC136313
0.8966	High Similarity	NPC120840
0.8966	High Similarity	NPC113989
0.8966	High Similarity	NPC46441
0.8966	High Similarity	NPC193750
0.8966	High Similarity	NPC49320
0.8953	High Similarity	NPC474511
0.8953	High Similarity	NPC1753
0.8941	High Similarity	NPC73038
0.8941	High Similarity	NPC235341
0.8941	High Similarity	NPC477579
0.8941	High Similarity	NPC155011
0.8941	High Similarity	NPC74363
0.8941	High Similarity	NPC325594
0.8941	High Similarity	NPC95594
0.8941	High Similarity	NPC475862
0.8941	High Similarity	NPC213412
0.8916	High Similarity	NPC69101
0.8916	High Similarity	NPC73882
0.8916	High Similarity	NPC310989
0.8916	High Similarity	NPC251779
0.8889	High Similarity	NPC9487
0.8889	High Similarity	NPC476318
0.8889	High Similarity	NPC327179
0.8889	High Similarity	NPC157113
0.8889	High Similarity	NPC204961
0.8889	High Similarity	NPC207922
0.8889	High Similarity	NPC259733
0.8889	High Similarity	NPC476327
0.8889	High Similarity	NPC132824
0.8889	High Similarity	NPC158371
0.8889	High Similarity	NPC173744
0.8889	High Similarity	NPC62516
0.8889	High Similarity	NPC88847
0.8889	High Similarity	NPC73004
0.8889	High Similarity	NPC116457
0.8876	High Similarity	NPC87095
0.8876	High Similarity	NPC88116
0.8876	High Similarity	NPC222047
0.8876	High Similarity	NPC20235
0.8876	High Similarity	NPC91010
0.8876	High Similarity	NPC474529
0.8876	High Similarity	NPC299996
0.8876	High Similarity	NPC231063
0.8876	High Similarity	NPC282395
0.8876	High Similarity	NPC145667
0.8876	High Similarity	NPC32407
0.8876	High Similarity	NPC263548
0.8864	High Similarity	NPC471588
0.8864	High Similarity	NPC235704
0.8864	High Similarity	NPC6255
0.8864	High Similarity	NPC475708
0.8851	High Similarity	NPC30522
0.8851	High Similarity	NPC281524
0.8837	High Similarity	NPC158141
0.8837	High Similarity	NPC187376
0.8837	High Similarity	NPC142361
0.8837	High Similarity	NPC474684
0.8837	High Similarity	NPC159046
0.8837	High Similarity	NPC173089
0.8837	High Similarity	NPC233836
0.8795	High Similarity	NPC3915
0.8795	High Similarity	NPC162632
0.8795	High Similarity	NPC267691
0.8795	High Similarity	NPC263272
0.8795	High Similarity	NPC274050
0.8791	High Similarity	NPC247139
0.8791	High Similarity	NPC9613
0.8791	High Similarity	NPC259788
0.8791	High Similarity	NPC43686
0.8791	High Similarity	NPC187933
0.8791	High Similarity	NPC189880
0.8791	High Similarity	NPC255589
0.878	High Similarity	NPC231431
0.878	High Similarity	NPC199595
0.878	High Similarity	NPC16394
0.8778	High Similarity	NPC148523
0.8778	High Similarity	NPC198245
0.8778	High Similarity	NPC195715

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 NPC71507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1566
0.2-0.3	3827
0.3-0.4	2385
0.4-0.5	707
0.5-0.6	212
0.6-0.7	203
0.7-0.8	67
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD7515	Phase 2
0.8667	High Similarity	NPD7748	Approved
0.8488	Intermediate Similarity	NPD4786	Approved
0.8471	Intermediate Similarity	NPD3667	Approved
0.8391	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7902	Approved
0.8222	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD6399	Phase 3
0.8118	Intermediate Similarity	NPD7645	Phase 2
0.809	Intermediate Similarity	NPD3618	Phase 1
0.8065	Intermediate Similarity	NPD7900	Approved
0.8065	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD5328	Approved
0.7912	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7849	Intermediate Similarity	NPD6079	Approved
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.766	Intermediate Similarity	NPD6411	Approved
0.766	Intermediate Similarity	NPD8034	Phase 2
0.766	Intermediate Similarity	NPD8035	Phase 2
0.7647	Intermediate Similarity	NPD6942	Approved
0.7647	Intermediate Similarity	NPD7339	Approved
0.7579	Intermediate Similarity	NPD4202	Approved
0.7558	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7638	Approved
0.7527	Intermediate Similarity	NPD6903	Approved
0.7526	Intermediate Similarity	NPD7614	Phase 1
0.75	Intermediate Similarity	NPD5279	Phase 3
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7128	Approved
0.7451	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD5739	Approved
0.7449	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD6083	Phase 2
0.7447	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6101	Approved
0.7419	Intermediate Similarity	NPD3573	Approved
0.7416	Intermediate Similarity	NPD7525	Registered
0.7416	Intermediate Similarity	NPD4695	Discontinued
0.7356	Intermediate Similarity	NPD6117	Approved
0.7347	Intermediate Similarity	NPD5221	Approved
0.7347	Intermediate Similarity	NPD5222	Approved
0.7347	Intermediate Similarity	NPD4697	Phase 3
0.7347	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6672	Approved
0.734	Intermediate Similarity	NPD5737	Approved
0.7326	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7273	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD5173	Approved
0.7263	Intermediate Similarity	NPD4753	Phase 2
0.7253	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD4221	Approved
0.7245	Intermediate Similarity	NPD5695	Phase 3
0.7238	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6373	Approved
0.7238	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD5697	Approved
0.7212	Intermediate Similarity	NPD5701	Approved
0.7204	Intermediate Similarity	NPD5329	Approved
0.7191	Intermediate Similarity	NPD6115	Approved
0.7191	Intermediate Similarity	NPD6118	Approved
0.7191	Intermediate Similarity	NPD6114	Approved
0.7191	Intermediate Similarity	NPD6697	Approved
0.7174	Intermediate Similarity	NPD4788	Approved
0.7172	Intermediate Similarity	NPD7732	Phase 3
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7129	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD4700	Approved
0.7129	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD6098	Approved
0.7113	Intermediate Similarity	NPD5284	Approved
0.7113	Intermediate Similarity	NPD5281	Approved
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD4197	Approved
0.7091	Intermediate Similarity	NPD7115	Discovery
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7041	Intermediate Similarity	NPD5778	Approved
0.7041	Intermediate Similarity	NPD5779	Approved
0.7037	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD8297	Approved
0.703	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD3617	Approved
0.699	Remote Similarity	NPD5226	Approved
0.699	Remote Similarity	NPD5224	Approved
0.699	Remote Similarity	NPD5211	Phase 2
0.699	Remote Similarity	NPD5225	Approved
0.699	Remote Similarity	NPD4633	Approved
0.6947	Remote Similarity	NPD4623	Approved
0.6947	Remote Similarity	NPD4693	Phase 3
0.6947	Remote Similarity	NPD4519	Discontinued
0.6947	Remote Similarity	NPD5280	Approved
0.6947	Remote Similarity	NPD4694	Approved
0.6947	Remote Similarity	NPD4689	Approved
0.6947	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD5690	Phase 2
0.6947	Remote Similarity	NPD4138	Approved
0.6947	Remote Similarity	NPD5205	Approved
0.6947	Remote Similarity	NPD4688	Approved
0.6947	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6926	Approved
0.6932	Remote Similarity	NPD6924	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD4754	Approved
0.6907	Remote Similarity	NPD6673	Approved
0.6907	Remote Similarity	NPD6080	Approved
0.6907	Remote Similarity	NPD6904	Approved
0.69	Remote Similarity	NPD5210	Approved
0.69	Remote Similarity	NPD4629	Approved
0.69	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6412	Phase 2
0.6882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8328	Phase 3
0.6863	Remote Similarity	NPD4225	Approved
0.686	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5141	Approved
0.6854	Remote Similarity	NPD8264	Approved
0.6848	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6868	Approved
0.6827	Remote Similarity	NPD7632	Discontinued
0.6818	Remote Similarity	NPD4632	Approved
0.6813	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5208	Approved
0.6792	Remote Similarity	NPD6008	Approved
0.6792	Remote Similarity	NPD4767	Approved
0.6792	Remote Similarity	NPD4768	Approved
0.6782	Remote Similarity	NPD4244	Approved
0.6782	Remote Similarity	NPD4245	Approved
0.6778	Remote Similarity	NPD6933	Approved
0.6774	Remote Similarity	NPD4139	Approved
0.6774	Remote Similarity	NPD4692	Approved
0.6768	Remote Similarity	NPD6050	Approved
0.6742	Remote Similarity	NPD4784	Approved
0.6742	Remote Similarity	NPD4785	Approved
0.6726	Remote Similarity	NPD6335	Approved
0.6706	Remote Similarity	NPD4224	Phase 2
0.6705	Remote Similarity	NPD7150	Approved
0.6705	Remote Similarity	NPD7152	Approved
0.6705	Remote Similarity	NPD7151	Approved
0.6705	Remote Similarity	NPD4243	Approved
0.6701	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD4748	Discontinued
0.6637	Remote Similarity	NPD6317	Approved
0.6637	Remote Similarity	NPD6009	Approved
0.6635	Remote Similarity	NPD6404	Discontinued
0.6634	Remote Similarity	NPD6001	Approved
0.6632	Remote Similarity	NPD5362	Discontinued
0.6606	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5694	Approved
0.66	Remote Similarity	NPD5693	Phase 1
0.66	Remote Similarity	NPD7637	Suspended
0.6596	Remote Similarity	NPD5369	Approved
0.6596	Remote Similarity	NPD8028	Phase 2

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