NPASS Compound

Structure

CID172361 OpenBabel06191715542D 33 37 0 0 1 0 0 0 0 0999 V2000 -1.8412 -4.0964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4293 -3.7805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -0.9737 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 -0.8432 1.4605 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 3.0165 2.3038 0.0000 C 0 0 0 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 0.8432 -1.4605 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 3.3729 -0.0000 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 -3.3729 -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 -2.5297 -0.4868 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 -1.6865 -2.9211 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 -1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3729 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0429 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 1 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 2.5297 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 3.1470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0692 2.3038 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 5 28 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 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 27 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 26 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 28 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 28 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 27 1 1 0 0 0 22 30 1 0 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 30 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	6.206
LogD:	4.856
LogS:	-5.062
# 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:	0.409
Synthetic Accessibility Score:	4.745
Fsp3:	0.9
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:	-5.297
MDCK Permeability:	2.4998882508953102e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.828

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	97.22644805908203%
Volume Distribution (VD):	0.877
Pgp-substrate:	3.040334463119507%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.344
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	2.051
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.769
Carcinogencity:	0.017
Eye Corrosion:	0.149
Eye Irritation:	0.719
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: NPC172361

Natural Product ID:	NPC172361
*Common Name:**	(3R,4R,4Ar,6Ar,6Bs,8Ar,12Ar,14Ar,14Br)-3-Hydroxy-4,6A,6B,8A,11,11,14B-Heptamethyl-1,2,3,4A,5,6,7,8,9,10,12,12A,14,14A-Tetradecahydropicene-4-Carboxylic Acid
IUPAC Name:	(3R,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	BZXULBWGROURAF-IKNLXHIFSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-25(2)14-15-26(3)16-17-28(5)19(20(26)18-25)8-9-21-27(4)12-11-23(31)30(7,24(32)33)22(27)10-13-29(21,28)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/p-1/t20-,21+,22+,23+,26+,27+,28+,29+,30+/m0/s1
SMILES:	CC1(C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H]([C@@](C)([C@@H]5CC[C@@]34C)C(=O)[O-])O)[C@@H]2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL395428
PubChem CID:	637234
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
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	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	12

Activity Type	# Activity
Individual Protein	8
Organism	3
Others	2
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	42000.0	nM	PMID[543208]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	48.7	%	PMID[543208]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Activity	=	100.0	%	PMID[543208]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	40000.0	nM	PMID[543208]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Activity	=	83.0	%	PMID[543208]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	40000.0	nM	PMID[543208]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Activity	=	85.1	%	PMID[543208]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	36.44	%	PMID[543205]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	25.8	%	PMID[543205]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	28.57	%	PMID[543205]
NPT614	Tissue	Plasma	Rattus norvegicus	FC	=	26.0	n.a.	PMID[543206]
NPT632	Tissue	Brain	Rattus norvegicus	Drug uptake	=	485.1	ng/g	PMID[543206]
NPT632	Tissue	Brain	Rattus norvegicus	Drug uptake	=	2443.9	ng/g	PMID[543206]
NPT27	Others	Unspecified		BPR	=	4.4	n.a.	PMID[543206]
NPT27	Others	Unspecified		BPR	=	0.18	n.a.	PMID[543206]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	1000.0	nM	PMID[543207]

☑ 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 NPC172361 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	207
0.1-0.2	1369
0.2-0.3	5117
0.3-0.4	13985
0.4-0.5	9285
0.5-0.6	5408
0.6-0.7	4664
0.7-0.8	2082
0.8-0.85	234
0.85-0.9	136
0.9-0.95	147
0.95-1	63

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86372
0.9882	High Similarity	NPC966
0.9882	High Similarity	NPC288833
0.9882	High Similarity	NPC228784
0.9882	High Similarity	NPC282616
0.9882	High Similarity	NPC155120
0.9882	High Similarity	NPC324341
0.9655	High Similarity	NPC222047
0.9651	High Similarity	NPC471588
0.9651	High Similarity	NPC6255
0.9647	High Similarity	NPC234346
0.9647	High Similarity	NPC121798
0.9647	High Similarity	NPC263393
0.9647	High Similarity	NPC130520
0.9647	High Similarity	NPC127689
0.9647	High Similarity	NPC61543
0.9647	High Similarity	NPC293048
0.9647	High Similarity	NPC225585
0.9647	High Similarity	NPC270768
0.9647	High Similarity	NPC59263
0.9643	High Similarity	NPC171203
0.9643	High Similarity	NPC102683
0.9643	High Similarity	NPC51700
0.9643	High Similarity	NPC88716
0.9643	High Similarity	NPC142415
0.9643	High Similarity	NPC242468
0.9643	High Similarity	NPC68160
0.9643	High Similarity	NPC18064
0.9643	High Similarity	NPC293564
0.9643	High Similarity	NPC98442
0.9643	High Similarity	NPC307426
0.9643	High Similarity	NPC130577
0.9545	High Similarity	NPC148523
0.954	High Similarity	NPC298554
0.9535	High Similarity	NPC111110
0.9535	High Similarity	NPC126369
0.9535	High Similarity	NPC470589
0.9535	High Similarity	NPC130278
0.9529	High Similarity	NPC182797
0.9529	High Similarity	NPC474512
0.9529	High Similarity	NPC181225
0.9529	High Similarity	NPC52169
0.9529	High Similarity	NPC40552
0.9529	High Similarity	NPC473242
0.9529	High Similarity	NPC17733
0.9529	High Similarity	NPC246708
0.9529	High Similarity	NPC470629
0.9529	High Similarity	NPC290690
0.9524	High Similarity	NPC72638
0.9438	High Similarity	NPC201657
0.9438	High Similarity	NPC132824
0.9438	High Similarity	NPC98874
0.9432	High Similarity	NPC184006
0.9432	High Similarity	NPC78580
0.9432	High Similarity	NPC209868
0.9432	High Similarity	NPC23621
0.9432	High Similarity	NPC474529
0.9419	High Similarity	NPC290972
0.9419	High Similarity	NPC64872
0.9419	High Similarity	NPC474972
0.9419	High Similarity	NPC470588
0.9419	High Similarity	NPC274330
0.9419	High Similarity	NPC25906
0.9419	High Similarity	NPC198664
0.9419	High Similarity	NPC95246
0.9419	High Similarity	NPC161751
0.9419	High Similarity	NPC143232
0.9333	High Similarity	NPC261935
0.9333	High Similarity	NPC106112
0.9326	High Similarity	NPC195715
0.9326	High Similarity	NPC23241
0.9318	High Similarity	NPC229281
0.9318	High Similarity	NPC86368
0.931	High Similarity	NPC273621
0.931	High Similarity	NPC210037
0.931	High Similarity	NPC290614
0.931	High Similarity	NPC7260
0.931	High Similarity	NPC227467
0.931	High Similarity	NPC18872
0.931	High Similarity	NPC291028
0.931	High Similarity	NPC120968
0.931	High Similarity	NPC477872
0.9294	High Similarity	NPC213412
0.9231	High Similarity	NPC29765
0.9231	High Similarity	NPC271614
0.9231	High Similarity	NPC174663
0.9231	High Similarity	NPC111214
0.9231	High Similarity	NPC164349
0.9213	High Similarity	NPC20235
0.9213	High Similarity	NPC231063
0.9213	High Similarity	NPC6818
0.9213	High Similarity	NPC282395
0.9213	High Similarity	NPC88116
0.9213	High Similarity	NPC145667
0.9213	High Similarity	NPC32407
0.9213	High Similarity	NPC191412
0.9213	High Similarity	NPC159365
0.9213	High Similarity	NPC114159
0.9213	High Similarity	NPC263548
0.9213	High Similarity	NPC299996
0.9205	High Similarity	NPC71074
0.9205	High Similarity	NPC300351
0.9205	High Similarity	NPC158030
0.9205	High Similarity	NPC187722
0.9205	High Similarity	NPC4036
0.9205	High Similarity	NPC145067
0.9205	High Similarity	NPC65120
0.9205	High Similarity	NPC235884
0.9205	High Similarity	NPC306541
0.9205	High Similarity	NPC105189
0.9205	High Similarity	NPC474525
0.9205	High Similarity	NPC475708
0.9205	High Similarity	NPC52021
0.9205	High Similarity	NPC84319
0.9205	High Similarity	NPC233455
0.9205	High Similarity	NPC472149
0.9205	High Similarity	NPC25299
0.9195	High Similarity	NPC474686
0.9195	High Similarity	NPC69627
0.9186	High Similarity	NPC71507
0.9186	High Similarity	NPC158141
0.9186	High Similarity	NPC173089
0.9176	High Similarity	NPC133954
0.913	High Similarity	NPC35239
0.9121	High Similarity	NPC26413
0.9121	High Similarity	NPC187933
0.9101	High Similarity	NPC272075
0.9101	High Similarity	NPC307335
0.9101	High Similarity	NPC295643
0.9101	High Similarity	NPC118490
0.9101	High Similarity	NPC158059
0.9101	High Similarity	NPC74855
0.9101	High Similarity	NPC63118
0.9101	High Similarity	NPC474436
0.9101	High Similarity	NPC118519
0.9101	High Similarity	NPC202728
0.9101	High Similarity	NPC49776
0.9101	High Similarity	NPC214756
0.9101	High Similarity	NPC136313
0.9101	High Similarity	NPC275809
0.9091	High Similarity	NPC474728
0.9091	High Similarity	NPC49320
0.9091	High Similarity	NPC46441
0.9091	High Similarity	NPC113989
0.9091	High Similarity	NPC193750
0.9091	High Similarity	NPC120840
0.908	High Similarity	NPC1753
0.908	High Similarity	NPC474511
0.907	High Similarity	NPC95594
0.907	High Similarity	NPC74363
0.907	High Similarity	NPC477579
0.907	High Similarity	NPC235341
0.907	High Similarity	NPC475862
0.9059	High Similarity	NPC171789
0.9022	High Similarity	NPC188833
0.9011	High Similarity	NPC73004
0.9011	High Similarity	NPC25848
0.9011	High Similarity	NPC476327
0.9011	High Similarity	NPC472806
0.9011	High Similarity	NPC476318
0.9011	High Similarity	NPC167193
0.9011	High Similarity	NPC173744
0.9011	High Similarity	NPC116457
0.9011	High Similarity	NPC19376
0.9011	High Similarity	NPC307282
0.9011	High Similarity	NPC204961
0.9011	High Similarity	NPC305464
0.9	High Similarity	NPC80365
0.9	High Similarity	NPC91010
0.9	High Similarity	NPC148964
0.8989	High Similarity	NPC301244
0.8989	High Similarity	NPC60755
0.8989	High Similarity	NPC77099
0.8989	High Similarity	NPC285184
0.8989	High Similarity	NPC470590
0.8989	High Similarity	NPC38754
0.8977	High Similarity	NPC30522
0.8966	High Similarity	NPC73064
0.8913	High Similarity	NPC476879
0.8913	High Similarity	NPC247139
0.8913	High Similarity	NPC476878
0.8913	High Similarity	NPC89225
0.8913	High Similarity	NPC9613
0.8913	High Similarity	NPC21728
0.8901	High Similarity	NPC32118
0.8901	High Similarity	NPC139570
0.8901	High Similarity	NPC198245
0.8901	High Similarity	NPC96916
0.8901	High Similarity	NPC474727
0.8901	High Similarity	NPC83693
0.8901	High Similarity	NPC473240
0.8889	High Similarity	NPC474806
0.8889	High Similarity	NPC133579
0.8864	High Similarity	NPC471900
0.8851	High Similarity	NPC325594
0.8851	High Similarity	NPC73038
0.8851	High Similarity	NPC9892
0.8851	High Similarity	NPC329943
0.8851	High Similarity	NPC91525
0.8851	High Similarity	NPC10005

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 NPC172361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1771
0.2-0.3	3863
0.3-0.4	2200
0.4-0.5	689
0.5-0.6	190
0.6-0.7	200
0.7-0.8	43
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9205	High Similarity	NPD7515	Phase 2
0.8791	High Similarity	NPD7748	Approved
0.8523	High Similarity	NPD7520	Clinical (unspecified phase)
0.8511	High Similarity	NPD7902	Approved
0.8471	Intermediate Similarity	NPD7645	Phase 2
0.8191	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7900	Approved
0.8022	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD4786	Approved
0.7978	Intermediate Similarity	NPD3667	Approved
0.7957	Intermediate Similarity	NPD5328	Approved
0.7789	Intermediate Similarity	NPD6411	Approved
0.7789	Intermediate Similarity	NPD6079	Approved
0.7789	Intermediate Similarity	NPD8034	Phase 2
0.7789	Intermediate Similarity	NPD8035	Phase 2
0.7708	Intermediate Similarity	NPD6399	Phase 3
0.766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3133	Approved
0.7609	Intermediate Similarity	NPD3666	Approved
0.7579	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6101	Approved
0.7573	Intermediate Similarity	NPD7128	Approved
0.7573	Intermediate Similarity	NPD5739	Approved
0.7573	Intermediate Similarity	NPD6402	Approved
0.7573	Intermediate Similarity	NPD6675	Approved
0.7526	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7434	Intermediate Similarity	NPD8328	Phase 3
0.7429	Intermediate Similarity	NPD6899	Approved
0.7429	Intermediate Similarity	NPD7320	Approved
0.7429	Intermediate Similarity	NPD6881	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD6084	Phase 2
0.74	Intermediate Similarity	NPD4755	Approved
0.7368	Intermediate Similarity	NPD3573	Approved
0.7364	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7115	Discovery
0.7363	Intermediate Similarity	NPD7525	Registered
0.7358	Intermediate Similarity	NPD6372	Approved
0.7358	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD5701	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7303	Intermediate Similarity	NPD6117	Approved
0.73	Intermediate Similarity	NPD5222	Approved
0.73	Intermediate Similarity	NPD4697	Phase 3
0.73	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD6903	Approved
0.729	Intermediate Similarity	NPD7102	Approved
0.729	Intermediate Similarity	NPD7290	Approved
0.729	Intermediate Similarity	NPD6883	Approved
0.7273	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5286	Approved
0.7255	Intermediate Similarity	NPD4700	Approved
0.7255	Intermediate Similarity	NPD4696	Approved
0.7255	Intermediate Similarity	NPD5285	Approved
0.7234	Intermediate Similarity	NPD3668	Phase 3
0.7228	Intermediate Similarity	NPD5173	Approved
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7222	Intermediate Similarity	NPD6650	Approved
0.7222	Intermediate Similarity	NPD8130	Phase 1
0.7222	Intermediate Similarity	NPD6847	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6617	Approved
0.7222	Intermediate Similarity	NPD6869	Approved
0.7216	Intermediate Similarity	NPD4753	Phase 2
0.7196	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD6014	Approved
0.7196	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6013	Approved
0.7191	Intermediate Similarity	NPD6942	Approved
0.7191	Intermediate Similarity	NPD7339	Approved
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD4225	Approved
0.7156	Intermediate Similarity	NPD8297	Approved
0.7156	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.7129	Intermediate Similarity	NPD7614	Phase 1
0.7115	Intermediate Similarity	NPD5225	Approved
0.7115	Intermediate Similarity	NPD4633	Approved
0.7115	Intermediate Similarity	NPD5224	Approved
0.7115	Intermediate Similarity	NPD5211	Phase 2
0.7115	Intermediate Similarity	NPD5226	Approved
0.7113	Intermediate Similarity	NPD5737	Approved
0.7113	Intermediate Similarity	NPD6672	Approved
0.7111	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6011	Approved
0.7083	Intermediate Similarity	NPD5279	Phase 3
0.7064	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5175	Approved
0.7048	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5695	Phase 3
0.7021	Intermediate Similarity	NPD4223	Phase 3
0.7021	Intermediate Similarity	NPD4221	Approved
0.7019	Intermediate Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD5696	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6981	Remote Similarity	NPD5141	Approved
0.6979	Remote Similarity	NPD5329	Approved
0.6972	Remote Similarity	NPD4634	Approved
0.6947	Remote Similarity	NPD4788	Approved
0.6916	Remote Similarity	NPD4767	Approved
0.6916	Remote Similarity	NPD4768	Approved
0.6907	Remote Similarity	NPD6098	Approved
0.6891	Remote Similarity	NPD7736	Approved
0.6887	Remote Similarity	NPD4754	Approved
0.6875	Remote Similarity	NPD4197	Approved
0.687	Remote Similarity	NPD6319	Approved
0.6863	Remote Similarity	NPD5210	Approved
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4629	Approved
0.6854	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6274	Approved
0.6814	Remote Similarity	NPD6868	Approved
0.6796	Remote Similarity	NPD7732	Phase 3
0.6792	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4729	Approved
0.6789	Remote Similarity	NPD4730	Approved
0.6789	Remote Similarity	NPD5128	Approved
0.6786	Remote Similarity	NPD4632	Approved
0.6783	Remote Similarity	NPD7100	Approved
0.6783	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD7492	Approved
0.6774	Remote Similarity	NPD3617	Approved
0.6735	Remote Similarity	NPD4693	Phase 3
0.6735	Remote Similarity	NPD4688	Approved
0.6735	Remote Similarity	NPD4138	Approved
0.6735	Remote Similarity	NPD4689	Approved
0.6735	Remote Similarity	NPD4623	Approved
0.6735	Remote Similarity	NPD4690	Approved
0.6735	Remote Similarity	NPD5205	Approved
0.6735	Remote Similarity	NPD4519	Discontinued
0.6733	Remote Similarity	NPD7637	Suspended
0.6733	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6054	Approved
0.6724	Remote Similarity	NPD6059	Approved
0.6723	Remote Similarity	NPD6616	Approved
0.67	Remote Similarity	NPD6080	Approved
0.67	Remote Similarity	NPD6673	Approved
0.67	Remote Similarity	NPD6904	Approved
0.6696	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD8133	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6633	Remote Similarity	NPD1694	Approved
0.663	Remote Similarity	NPD3703	Phase 2
0.661	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6609	Remote Similarity	NPD6317	Approved
0.6607	Remote Similarity	NPD5215	Approved
0.6607	Remote Similarity	NPD5217	Approved
0.6607	Remote Similarity	NPD5216	Approved
0.6606	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD6001	Approved
0.66	Remote Similarity	NPD5208	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7507	Approved
0.6566	Remote Similarity	NPD5280	Approved
0.6566	Remote Similarity	NPD4694	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6562	Remote Similarity	NPD5369	Approved
0.6556	Remote Similarity	NPD4244	Approved
0.6556	Remote Similarity	NPD4245	Approved
0.6552	Remote Similarity	NPD6313	Approved
0.6552	Remote Similarity	NPD6314	Approved
0.6525	Remote Similarity	NPD6015	Approved
0.6525	Remote Similarity	NPD6016	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