NPASS Compound

Structure

CID300324 OpenBabel06191716102D 31 34 0 0 1 0 0 0 0 0999 V2000 1.4598 -5.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9983 -5.1980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2724 -3.2187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3725 2.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5597 -0.5051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2067 -3.4215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6354 -4.2084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8109 -2.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6867 1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3717 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.4599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2143 0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6850 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6859 -0.9733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8427 -1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0311 -5.0967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8435 -1.4594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5296 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5294 0.4860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2146 1.4590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3723 1.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6861 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0808 1.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 2 0 0 0 0 13 15 1 0 0 0 0 13 24 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 22 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 21 3 1 1 0 0 0 21 22 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 6 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 26 31 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	496.727
LogP:	8.344
LogD:	6.159
LogS:	-6.853
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.664
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	8.18132593849441e-06
Pgp-inhibitor:	0.029
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	94.14244079589844%
Volume Distribution (VD):	2.203
Pgp-substrate:	1.6455134153366089%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.213
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.559

ADMET: Excretion

Clearance (CL):	10.537
Half-life (T1/2):	0.017

ADMET: Toxicity

hERG Blockers:	0.303
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.453
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.741
Carcinogencity:	0.103
Eye Corrosion:	0.111
Eye Irritation:	0.122
Respiratory Toxicity:	0.743

Download Data

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

Natural Product: NPC300324

Natural Product ID:	NPC300324
*Common Name:**	10Alpha-Cucurbitadienol
IUPAC Name:	(3S,8R,9R,10S,13R,14S,17R)-4,4,9,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	10Alpha-Cucurbitadienol
Standard InCHIKey:	WSPRAEIJBDUDRX-FBJXRMALSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-16-17-30(8)25-14-12-23-24(13-15-26(31)27(23,4)5)28(25,6)18-19-29(22,30)7/h10,12,21-22,24-26,31H,9,11,13-19H2,1-8H3/t21-,22-,24-,25-,26+,28+,29-,30+/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC=C4[C@@H](CC[C@@H](C4(C)C)O)[C@]3(C)CC[C@]12C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497823
PubChem CID:	14543446
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO31363	Rhus sylvestris	Species	Anacardiaceae	Eukaryota	stems and leaves	n.a.	n.a.	PMID[19447618]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	3
Others	1

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	80.9	%	PMID[567188]
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	>	50000.0	nM	PMID[567188]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[567188]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[567188]

☑ 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 NPC300324 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	157
0.1-0.2	1405
0.2-0.3	7469
0.3-0.4	15878
0.4-0.5	6840
0.5-0.6	5525
0.6-0.7	3836
0.7-0.8	1167
0.8-0.85	234
0.85-0.9	105
0.9-0.95	56
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC240604
0.9857	High Similarity	NPC230301
0.9857	High Similarity	NPC304309
0.9857	High Similarity	NPC28657
0.9857	High Similarity	NPC162742
0.9857	High Similarity	NPC136188
0.9857	High Similarity	NPC288035
0.9857	High Similarity	NPC285893
0.9857	High Similarity	NPC134847
0.9857	High Similarity	NPC22105
0.9718	High Similarity	NPC321016
0.9718	High Similarity	NPC189883
0.9718	High Similarity	NPC113733
0.9718	High Similarity	NPC321381
0.9718	High Similarity	NPC107059
0.9583	High Similarity	NPC34019
0.9583	High Similarity	NPC155986
0.9583	High Similarity	NPC198968
0.9583	High Similarity	NPC318495
0.9577	High Similarity	NPC471723
0.9577	High Similarity	NPC141071
0.9577	High Similarity	NPC257347
0.9452	High Similarity	NPC474216
0.9452	High Similarity	NPC76931
0.9452	High Similarity	NPC477522
0.9452	High Similarity	NPC473943
0.9452	High Similarity	NPC87604
0.9452	High Similarity	NPC18603
0.9452	High Similarity	NPC307965
0.9452	High Similarity	NPC275910
0.9444	High Similarity	NPC129165
0.9444	High Similarity	NPC202642
0.9444	High Similarity	NPC134330
0.9444	High Similarity	NPC237460
0.9444	High Similarity	NPC46160
0.9333	High Similarity	NPC474531
0.9333	High Similarity	NPC470383
0.9324	High Similarity	NPC328714
0.9324	High Similarity	NPC1319
0.9324	High Similarity	NPC28862
0.9324	High Similarity	NPC47982
0.9324	High Similarity	NPC81306
0.9324	High Similarity	NPC109546
0.9324	High Similarity	NPC143182
0.9324	High Similarity	NPC84694
0.9315	High Similarity	NPC214570
0.9306	High Similarity	NPC121744
0.9306	High Similarity	NPC322353
0.9306	High Similarity	NPC118508
0.9211	High Similarity	NPC49964
0.9211	High Similarity	NPC101462
0.92	High Similarity	NPC236112
0.92	High Similarity	NPC241290
0.92	High Similarity	NPC209944
0.92	High Similarity	NPC26117
0.92	High Similarity	NPC234193
0.92	High Similarity	NPC164840
0.9189	High Similarity	NPC285761
0.9189	High Similarity	NPC167037
0.9189	High Similarity	NPC65897
0.9189	High Similarity	NPC85346
0.9189	High Similarity	NPC138621
0.9189	High Similarity	NPC205455
0.9189	High Similarity	NPC186191
0.9189	High Similarity	NPC244385
0.9189	High Similarity	NPC302041
0.9189	High Similarity	NPC6978
0.9178	High Similarity	NPC244488
0.9178	High Similarity	NPC96319
0.9178	High Similarity	NPC73875
0.9178	High Similarity	NPC470362
0.9178	High Similarity	NPC247325
0.9079	High Similarity	NPC47761
0.9079	High Similarity	NPC474759
0.9079	High Similarity	NPC23852
0.9079	High Similarity	NPC7505
0.9079	High Similarity	NPC264245
0.9079	High Similarity	NPC474731
0.9079	High Similarity	NPC474752
0.9079	High Similarity	NPC209620
0.9079	High Similarity	NPC474683
0.9079	High Similarity	NPC82986
0.9067	High Similarity	NPC273410
0.9067	High Similarity	NPC30986
0.9067	High Similarity	NPC209430
0.9067	High Similarity	NPC80530
0.9028	High Similarity	NPC201373
0.9028	High Similarity	NPC474140
0.9028	High Similarity	NPC471799
0.9028	High Similarity	NPC182717
0.9	High Similarity	NPC160209
0.9	High Similarity	NPC208999
0.8974	High Similarity	NPC205845
0.8974	High Similarity	NPC185568
0.8974	High Similarity	NPC209802
0.8974	High Similarity	NPC124172
0.8961	High Similarity	NPC470049
0.8961	High Similarity	NPC470614
0.8961	High Similarity	NPC248886
0.8961	High Similarity	NPC1272
0.8961	High Similarity	NPC189972
0.8961	High Similarity	NPC30166
0.8961	High Similarity	NPC201852
0.8961	High Similarity	NPC50964
0.8961	High Similarity	NPC5985
0.8947	High Similarity	NPC13554
0.8947	High Similarity	NPC322313
0.8947	High Similarity	NPC102253
0.8947	High Similarity	NPC236237
0.8933	High Similarity	NPC318136
0.8933	High Similarity	NPC477514
0.8933	High Similarity	NPC312328
0.8919	High Similarity	NPC106364
0.8904	High Similarity	NPC469593
0.8904	High Similarity	NPC477138
0.8904	High Similarity	NPC471797
0.8904	High Similarity	NPC243342
0.8904	High Similarity	NPC100334
0.8904	High Similarity	NPC469533
0.8904	High Similarity	NPC469534
0.8889	High Similarity	NPC111234
0.8861	High Similarity	NPC157257
0.8861	High Similarity	NPC274448
0.8861	High Similarity	NPC266511
0.8846	High Similarity	NPC317458
0.8846	High Similarity	NPC475789
0.8846	High Similarity	NPC474634
0.8816	High Similarity	NPC472463
0.88	High Similarity	NPC471798
0.8784	High Similarity	NPC291503
0.8784	High Similarity	NPC66566
0.8784	High Similarity	NPC477923
0.8784	High Similarity	NPC471468
0.875	High Similarity	NPC474970
0.875	High Similarity	NPC475728
0.875	High Similarity	NPC6391
0.875	High Similarity	NPC94462
0.875	High Similarity	NPC45296
0.875	High Similarity	NPC24277
0.875	High Similarity	NPC145498
0.875	High Similarity	NPC261266
0.8734	High Similarity	NPC221758
0.8734	High Similarity	NPC59453
0.8734	High Similarity	NPC472265
0.8734	High Similarity	NPC33913
0.8734	High Similarity	NPC478102
0.8734	High Similarity	NPC470077
0.8718	High Similarity	NPC87489
0.8718	High Similarity	NPC218616
0.8718	High Similarity	NPC296701
0.8718	High Similarity	NPC20853
0.8718	High Similarity	NPC202389
0.8684	High Similarity	NPC474989
0.8684	High Similarity	NPC22955
0.8684	High Similarity	NPC99168
0.8684	High Similarity	NPC470396
0.8667	High Similarity	NPC122418
0.8667	High Similarity	NPC265328
0.8667	High Similarity	NPC290598
0.8667	High Similarity	NPC27765
0.8667	High Similarity	NPC30590
0.8667	High Similarity	NPC120098
0.8649	High Similarity	NPC145552
0.8649	High Similarity	NPC254509
0.8649	High Similarity	NPC329090
0.8649	High Similarity	NPC196358
0.8649	High Similarity	NPC192638
0.8649	High Similarity	NPC25511
0.8649	High Similarity	NPC91858
0.8649	High Similarity	NPC49168
0.8649	High Similarity	NPC62657
0.8649	High Similarity	NPC5046
0.8649	High Similarity	NPC27395
0.8642	High Similarity	NPC475313
0.8642	High Similarity	NPC475740
0.8642	High Similarity	NPC149224
0.863	High Similarity	NPC242001
0.863	High Similarity	NPC167706
0.863	High Similarity	NPC110799
0.8625	High Similarity	NPC474349
0.8625	High Similarity	NPC318390
0.8625	High Similarity	NPC474189
0.8611	High Similarity	NPC269877
0.8611	High Similarity	NPC167272
0.8608	High Similarity	NPC113978
0.8608	High Similarity	NPC477818
0.8608	High Similarity	NPC207013
0.8608	High Similarity	NPC110778
0.8592	High Similarity	NPC197805
0.859	High Similarity	NPC6707
0.8571	High Similarity	NPC53744
0.8571	High Similarity	NPC291379
0.8553	High Similarity	NPC91594
0.8553	High Similarity	NPC34177
0.8553	High Similarity	NPC477924
0.8553	High Similarity	NPC472805
0.8553	High Similarity	NPC101475
0.8553	High Similarity	NPC90979
0.8553	High Similarity	NPC157996
0.8553	High Similarity	NPC40394

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 NPC300324 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1660
0.2-0.3	4482
0.3-0.4	1991
0.4-0.5	424
0.5-0.6	167
0.6-0.7	152
0.7-0.8	77
0.8-0.85	13
0.85-0.9	15
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9857	High Similarity	NPD7339	Approved
0.9857	High Similarity	NPD6942	Approved
0.9178	High Similarity	NPD3701	Clinical (unspecified phase)
0.8947	High Similarity	NPD7525	Registered
0.8734	High Similarity	NPD4786	Approved
0.8649	High Similarity	NPD6926	Approved
0.8649	High Similarity	NPD4784	Approved
0.8649	High Similarity	NPD6924	Approved
0.8649	High Similarity	NPD4785	Approved
0.863	High Similarity	NPD7150	Approved
0.863	High Similarity	NPD7151	Approved
0.863	High Similarity	NPD7152	Approved
0.863	High Similarity	NPD4243	Approved
0.8611	High Similarity	NPD6922	Approved
0.8611	High Similarity	NPD6923	Approved
0.8493	Intermediate Similarity	NPD7143	Approved
0.8493	Intermediate Similarity	NPD7144	Approved
0.8481	Intermediate Similarity	NPD3667	Approved
0.8421	Intermediate Similarity	NPD6933	Approved
0.8333	Intermediate Similarity	NPD7645	Phase 2
0.8214	Intermediate Similarity	NPD5328	Approved
0.8193	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6929	Approved
0.8072	Intermediate Similarity	NPD3618	Phase 1
0.8052	Intermediate Similarity	NPD5275	Approved
0.8052	Intermediate Similarity	NPD4190	Phase 3
0.8023	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD4748	Discontinued
0.8	Intermediate Similarity	NPD6931	Approved
0.8	Intermediate Similarity	NPD6930	Phase 2
0.7848	Intermediate Similarity	NPD6932	Approved
0.7848	Intermediate Similarity	NPD5776	Phase 2
0.7848	Intermediate Similarity	NPD6925	Approved
0.7831	Intermediate Similarity	NPD3666	Approved
0.7831	Intermediate Similarity	NPD3133	Approved
0.7831	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD7509	Discontinued
0.775	Intermediate Similarity	NPD7145	Approved
0.7727	Intermediate Similarity	NPD6399	Phase 3
0.7727	Intermediate Similarity	NPD4202	Approved
0.7711	Intermediate Similarity	NPD6695	Phase 3
0.7654	Intermediate Similarity	NPD6683	Phase 2
0.7654	Intermediate Similarity	NPD4195	Approved
0.7619	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3668	Phase 3
0.7561	Intermediate Similarity	NPD7514	Phase 3
0.7531	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6893	Approved
0.7473	Intermediate Similarity	NPD5221	Approved
0.7473	Intermediate Similarity	NPD5222	Approved
0.7473	Intermediate Similarity	NPD4697	Phase 3
0.7473	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6902	Approved
0.7442	Intermediate Similarity	NPD5279	Phase 3
0.7391	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD5173	Approved
0.7386	Intermediate Similarity	NPD4753	Phase 2
0.7381	Intermediate Similarity	NPD4221	Approved
0.7381	Intermediate Similarity	NPD4223	Phase 3
0.7375	Intermediate Similarity	NPD8264	Approved
0.7356	Intermediate Similarity	NPD7524	Approved
0.7356	Intermediate Similarity	NPD7750	Discontinued
0.7349	Intermediate Similarity	NPD7332	Phase 2
0.7326	Intermediate Similarity	NPD5329	Approved
0.7262	Intermediate Similarity	NPD6898	Phase 1
0.7234	Intermediate Similarity	NPD4696	Approved
0.7234	Intermediate Similarity	NPD5285	Approved
0.7234	Intermediate Similarity	NPD5286	Approved
0.7234	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7209	Intermediate Similarity	NPD4197	Approved
0.7179	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5223	Approved
0.7128	Intermediate Similarity	NPD7638	Approved
0.7128	Intermediate Similarity	NPD5290	Discontinued
0.7093	Intermediate Similarity	NPD4788	Approved
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7083	Intermediate Similarity	NPD5226	Approved
0.7083	Intermediate Similarity	NPD5224	Approved
0.7083	Intermediate Similarity	NPD4633	Approved
0.7083	Intermediate Similarity	NPD5225	Approved
0.7053	Intermediate Similarity	NPD7640	Approved
0.7053	Intermediate Similarity	NPD7639	Approved
0.7045	Intermediate Similarity	NPD5205	Approved
0.7045	Intermediate Similarity	NPD4138	Approved
0.7045	Intermediate Similarity	NPD5330	Approved
0.7045	Intermediate Similarity	NPD6409	Approved
0.7045	Intermediate Similarity	NPD4689	Approved
0.7045	Intermediate Similarity	NPD4688	Approved
0.7045	Intermediate Similarity	NPD7146	Approved
0.7045	Intermediate Similarity	NPD6684	Approved
0.7045	Intermediate Similarity	NPD4690	Approved
0.7045	Intermediate Similarity	NPD4693	Phase 3
0.7045	Intermediate Similarity	NPD7521	Approved
0.7045	Intermediate Similarity	NPD7334	Approved
0.7041	Intermediate Similarity	NPD6675	Approved
0.7041	Intermediate Similarity	NPD5739	Approved
0.7041	Intermediate Similarity	NPD6402	Approved
0.7041	Intermediate Similarity	NPD7128	Approved
0.7033	Intermediate Similarity	NPD7087	Discontinued
0.7021	Intermediate Similarity	NPD6083	Phase 2
0.7021	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD5174	Approved
0.701	Intermediate Similarity	NPD5175	Approved
0.701	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.6989	Remote Similarity	NPD4629	Approved
0.6989	Remote Similarity	NPD5210	Approved
0.6939	Remote Similarity	NPD5141	Approved
0.6905	Remote Similarity	NPD3617	Approved
0.69	Remote Similarity	NPD7320	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.6889	Remote Similarity	NPD5737	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6672	Approved
0.6889	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD4723	Approved
0.6889	Remote Similarity	NPD4722	Approved
0.6882	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD4787	Phase 1
0.6869	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD4768	Approved
0.6854	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5280	Approved
0.6854	Remote Similarity	NPD4694	Approved
0.6854	Remote Similarity	NPD5690	Phase 2
0.6848	Remote Similarity	NPD8035	Phase 2
0.6848	Remote Similarity	NPD8034	Phase 2
0.6832	Remote Similarity	NPD6373	Approved
0.6832	Remote Similarity	NPD6372	Approved
0.68	Remote Similarity	NPD5697	Approved
0.68	Remote Similarity	NPD5701	Approved
0.679	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.6744	Remote Similarity	NPD4695	Discontinued
0.6733	Remote Similarity	NPD5128	Approved
0.6733	Remote Similarity	NPD4730	Approved
0.6733	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD5168	Approved
0.6733	Remote Similarity	NPD4729	Approved
0.6711	Remote Similarity	NPD368	Approved
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6633	Remote Similarity	NPD4159	Approved
0.6632	Remote Similarity	NPD5695	Phase 3
0.6627	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5251	Approved
0.6602	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5250	Approved
0.6602	Remote Similarity	NPD5249	Phase 3
0.6602	Remote Similarity	NPD5247	Approved
0.6602	Remote Similarity	NPD5248	Approved
0.6602	Remote Similarity	NPD5169	Approved
0.6602	Remote Similarity	NPD5135	Approved
0.6602	Remote Similarity	NPD4634	Approved
0.6598	Remote Similarity	NPD5696	Approved
0.6588	Remote Similarity	NPD6116	Phase 1
0.6575	Remote Similarity	NPD342	Phase 1
0.6559	Remote Similarity	NPD7136	Phase 2
0.6543	Remote Similarity	NPD4137	Phase 3
0.6543	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD5216	Approved
0.6538	Remote Similarity	NPD5127	Approved
0.6538	Remote Similarity	NPD5215	Approved
0.6538	Remote Similarity	NPD5217	Approved
0.6512	Remote Similarity	NPD6114	Approved
0.6512	Remote Similarity	NPD6697	Approved
0.6512	Remote Similarity	NPD6118	Approved
0.6512	Remote Similarity	NPD6115	Approved
0.6489	Remote Similarity	NPD5281	Approved
0.6489	Remote Similarity	NPD5284	Approved
0.6484	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD6412	Phase 2
0.6463	Remote Similarity	NPD6938	Clinical (unspecified phase)

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