NPASS Compound

Structure

CID251929 OpenBabel06191716052D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.7220 1.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5148 -0.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 1.4506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6773 -2.9025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 -2.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6765 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3526 -0.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3531 -2.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 -0.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5154 -2.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1907 -2.4179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 -1.4510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8384 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 -0.9668 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6753 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5151 -1.4505 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 5.0568 -2.9176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5414 0.4993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 4 16 2 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 15 6 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 1 0 0 0 18 21 1 1 0 0 0 19 23 2 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.21
Volume:	344.581
LogP:	3.541
LogD:	3.305
LogS:	-4.424
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	4.384
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	2.540586137911305e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.366
30% Bioavailability (F30%):	0.79

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	87.69567108154297%
Volume Distribution (VD):	0.564
Pgp-substrate:	5.368531703948975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.551
CYP2C19-inhibitor:	0.636
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.261
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.52

ADMET: Excretion

Clearance (CL):	7.739
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.277
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.421
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.918
Carcinogencity:	0.885
Eye Corrosion:	0.238
Eye Irritation:	0.105
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC251929

Natural Product ID:	NPC251929
*Common Name:**	(8S,9R,10R,13S,14R,17E)-17-Ethylidene-10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15-Decahydrocyclopenta[A]Phenanthrene-3,16-Dione
IUPAC Name:	(8S,9R,10R,13S,14R,17E)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
Synonyms:
Standard InCHIKey:	WDXRGPWQVHZTQJ-DWPFYVIESA-N
Standard InCHI:	InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4-/t15-,17+,18+,20-,21+/m0/s1
SMILES:	C/C=C1/C(=O)C[C@H]2[C@]1(C)CC[C@@H]1[C@@H]2CCC2=CC(=O)CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1514005
PubChem CID:	16759145
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids [CHEMONTID:0001467] Androgens and derivatives

*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
NPO13567	Streptomyces sahachiroi	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20485749]
NPO13567	Streptomyces sahachiroi	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16197	Eucalyptus microcorys	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16527	Baptisia minor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13402	Eupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16488	Achromobacter piechaudii	Species	Alcaligenaceae	Bacteria	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
Potency	5

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	100.0	nM	PMID[487680]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[487680]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[487680]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[487680]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	28183.8	nM	PMID[487680]

☑ 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 NPC251929 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	168
0.1-0.2	1908
0.2-0.3	11027
0.3-0.4	13617
0.4-0.5	7502
0.5-0.6	5488
0.6-0.7	2350
0.7-0.8	525
0.8-0.85	67
0.85-0.9	16
0.9-0.95	16
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC2634
1.0	High Similarity	NPC265782
0.9848	High Similarity	NPC54123
0.9846	High Similarity	NPC139397
0.9701	High Similarity	NPC474228
0.9701	High Similarity	NPC303613
0.9697	High Similarity	NPC307176
0.9697	High Similarity	NPC260040
0.9412	High Similarity	NPC251705
0.9403	High Similarity	NPC35734
0.9403	High Similarity	NPC159577
0.9403	High Similarity	NPC282593
0.9286	High Similarity	NPC69408
0.9275	High Similarity	NPC309852
0.9275	High Similarity	NPC255021
0.9265	High Similarity	NPC305501
0.9265	High Similarity	NPC234707
0.9265	High Similarity	NPC115023
0.9143	High Similarity	NPC293803
0.913	High Similarity	NPC470044
0.913	High Similarity	NPC470045
0.9104	High Similarity	NPC188292
0.9104	High Similarity	NPC20610
0.9104	High Similarity	NPC260474
0.9091	High Similarity	NPC323005
0.9077	High Similarity	NPC212210
0.9	High Similarity	NPC474796
0.9	High Similarity	NPC474797
0.9	High Similarity	NPC329866
0.8971	High Similarity	NPC182815
0.8873	High Similarity	NPC473171
0.8873	High Similarity	NPC255650
0.8824	High Similarity	NPC310992
0.8824	High Similarity	NPC87141
0.8806	High Similarity	NPC92327
0.8788	High Similarity	NPC469662
0.8784	High Similarity	NPC474509
0.875	High Similarity	NPC469796
0.875	High Similarity	NPC469793
0.8714	High Similarity	NPC470078
0.8714	High Similarity	NPC5701
0.8714	High Similarity	NPC190035
0.8696	High Similarity	NPC256846
0.8676	High Similarity	NPC176107
0.8676	High Similarity	NPC475523
0.8657	High Similarity	NPC251118
0.8649	High Similarity	NPC90965
0.8649	High Similarity	NPC170793
0.8636	High Similarity	NPC202118
0.8636	High Similarity	NPC165695
0.8636	High Similarity	NPC197238
0.8615	High Similarity	NPC127582
0.8571	High Similarity	NPC40574
0.8571	High Similarity	NPC214770
0.8571	High Similarity	NPC477856
0.8553	High Similarity	NPC472239
0.8551	High Similarity	NPC155198
0.8507	High Similarity	NPC475124
0.8507	High Similarity	NPC285371
0.8485	Intermediate Similarity	NPC213152
0.8462	Intermediate Similarity	NPC472304
0.8462	Intermediate Similarity	NPC259261
0.8462	Intermediate Similarity	NPC276764
0.8451	Intermediate Similarity	NPC181204
0.8451	Intermediate Similarity	NPC223187
0.8451	Intermediate Similarity	NPC225467
0.8429	Intermediate Similarity	NPC286814
0.8429	Intermediate Similarity	NPC477857
0.8358	Intermediate Similarity	NPC32285
0.8358	Intermediate Similarity	NPC288253
0.8333	Intermediate Similarity	NPC25853
0.8312	Intermediate Similarity	NPC320514
0.8312	Intermediate Similarity	NPC472867
0.8312	Intermediate Similarity	NPC142253
0.8312	Intermediate Similarity	NPC193347
0.8312	Intermediate Similarity	NPC3511
0.8308	Intermediate Similarity	NPC94991
0.8308	Intermediate Similarity	NPC266295
0.8308	Intermediate Similarity	NPC27610
0.8308	Intermediate Similarity	NPC56905
0.8289	Intermediate Similarity	NPC472478
0.8286	Intermediate Similarity	NPC142754
0.8286	Intermediate Similarity	NPC82477
0.8286	Intermediate Similarity	NPC39157
0.8286	Intermediate Similarity	NPC296697
0.8267	Intermediate Similarity	NPC470052
0.8267	Intermediate Similarity	NPC115515
0.8267	Intermediate Similarity	NPC82635
0.8267	Intermediate Similarity	NPC469996
0.8261	Intermediate Similarity	NPC176171
0.8243	Intermediate Similarity	NPC474463
0.8243	Intermediate Similarity	NPC1254
0.8228	Intermediate Similarity	NPC29447
0.8219	Intermediate Similarity	NPC219232
0.8219	Intermediate Similarity	NPC128346
0.8219	Intermediate Similarity	NPC211641
0.8209	Intermediate Similarity	NPC60565
0.8194	Intermediate Similarity	NPC474562
0.8143	Intermediate Similarity	NPC4370
0.8143	Intermediate Similarity	NPC290350
0.8143	Intermediate Similarity	NPC220210
0.8143	Intermediate Similarity	NPC20181
0.8133	Intermediate Similarity	NPC472300
0.8133	Intermediate Similarity	NPC91665
0.8108	Intermediate Similarity	NPC476346
0.8101	Intermediate Similarity	NPC87552
0.8101	Intermediate Similarity	NPC161423
0.8101	Intermediate Similarity	NPC237712
0.8101	Intermediate Similarity	NPC144258
0.8101	Intermediate Similarity	NPC227064
0.8101	Intermediate Similarity	NPC85774
0.8101	Intermediate Similarity	NPC329043
0.8101	Intermediate Similarity	NPC181743
0.8101	Intermediate Similarity	NPC178025
0.8101	Intermediate Similarity	NPC58841
0.8101	Intermediate Similarity	NPC321187
0.8101	Intermediate Similarity	NPC214043
0.8101	Intermediate Similarity	NPC16287
0.8088	Intermediate Similarity	NPC472306
0.8082	Intermediate Similarity	NPC56747
0.8082	Intermediate Similarity	NPC474488
0.8082	Intermediate Similarity	NPC180015
0.8082	Intermediate Similarity	NPC130016
0.8082	Intermediate Similarity	NPC109576
0.8077	Intermediate Similarity	NPC469806
0.8077	Intermediate Similarity	NPC469804
0.8077	Intermediate Similarity	NPC100297
0.8077	Intermediate Similarity	NPC469805
0.8077	Intermediate Similarity	NPC469799
0.8052	Intermediate Similarity	NPC469798
0.8052	Intermediate Similarity	NPC469797
0.8052	Intermediate Similarity	NPC476809
0.803	Intermediate Similarity	NPC60772
0.803	Intermediate Similarity	NPC30215
0.803	Intermediate Similarity	NPC311852
0.8026	Intermediate Similarity	NPC228911
0.8026	Intermediate Similarity	NPC189485
0.8025	Intermediate Similarity	NPC93778
0.8	Intermediate Similarity	NPC168824
0.8	Intermediate Similarity	NPC469948
0.8	Intermediate Similarity	NPC323765
0.8	Intermediate Similarity	NPC39462
0.8	Intermediate Similarity	NPC60350
0.8	Intermediate Similarity	NPC189917
0.8	Intermediate Similarity	NPC43300
0.8	Intermediate Similarity	NPC96812
0.8	Intermediate Similarity	NPC107704
0.8	Intermediate Similarity	NPC8571
0.7975	Intermediate Similarity	NPC474976
0.7975	Intermediate Similarity	NPC41539
0.7975	Intermediate Similarity	NPC3856
0.7975	Intermediate Similarity	NPC474790
0.7975	Intermediate Similarity	NPC279639
0.7973	Intermediate Similarity	NPC20025
0.7973	Intermediate Similarity	NPC159497
0.7971	Intermediate Similarity	NPC473902
0.7971	Intermediate Similarity	NPC6697
0.7949	Intermediate Similarity	NPC278459
0.7949	Intermediate Similarity	NPC147066
0.7949	Intermediate Similarity	NPC477372
0.7945	Intermediate Similarity	NPC133253
0.7945	Intermediate Similarity	NPC21944
0.7945	Intermediate Similarity	NPC304983
0.7941	Intermediate Similarity	NPC475795
0.7941	Intermediate Similarity	NPC97322
0.7922	Intermediate Similarity	NPC27817
0.7922	Intermediate Similarity	NPC472490
0.7922	Intermediate Similarity	NPC190211
0.7922	Intermediate Similarity	NPC215843
0.7922	Intermediate Similarity	NPC476177
0.7901	Intermediate Similarity	NPC474732
0.7901	Intermediate Similarity	NPC31564
0.7901	Intermediate Similarity	NPC195640
0.7901	Intermediate Similarity	NPC145879
0.7901	Intermediate Similarity	NPC474733
0.7901	Intermediate Similarity	NPC327115
0.7901	Intermediate Similarity	NPC474778
0.7895	Intermediate Similarity	NPC470557
0.7895	Intermediate Similarity	NPC165711
0.7879	Intermediate Similarity	NPC49575
0.7879	Intermediate Similarity	NPC55004
0.7879	Intermediate Similarity	NPC230823
0.7879	Intermediate Similarity	NPC115385
0.7879	Intermediate Similarity	NPC267626
0.7875	Intermediate Similarity	NPC473246
0.7867	Intermediate Similarity	NPC469803
0.7867	Intermediate Similarity	NPC65650
0.7857	Intermediate Similarity	NPC470329
0.7848	Intermediate Similarity	NPC327969
0.7848	Intermediate Similarity	NPC321289
0.7848	Intermediate Similarity	NPC151519
0.7848	Intermediate Similarity	NPC328351
0.7831	Intermediate Similarity	NPC262043
0.7821	Intermediate Similarity	NPC2482
0.7821	Intermediate Similarity	NPC108955
0.7808	Intermediate Similarity	NPC246722
0.7808	Intermediate Similarity	NPC151045
0.7805	Intermediate Similarity	NPC136948
0.7805	Intermediate Similarity	NPC58063
0.7805	Intermediate Similarity	NPC475740

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 NPC251929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1978
0.2-0.3	4586
0.3-0.4	1727
0.4-0.5	337
0.5-0.6	132
0.6-0.7	138
0.7-0.8	66
0.8-0.85	15
0.85-0.9	3
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4691	Approved
0.9846	High Similarity	NPD4137	Phase 3
0.9697	High Similarity	NPD4747	Approved
0.9559	High Similarity	NPD4058	Approved
0.9104	High Similarity	NPD3621	Clinical (unspecified phase)
0.9	High Similarity	NPD5733	Approved
0.9	High Similarity	NPD4687	Approved
0.8986	High Similarity	NPD5276	Approved
0.8312	Intermediate Similarity	NPD4223	Phase 3
0.8312	Intermediate Similarity	NPD4221	Approved
0.8205	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3133	Approved
0.8101	Intermediate Similarity	NPD3666	Approved
0.8101	Intermediate Similarity	NPD3665	Phase 1
0.8101	Intermediate Similarity	NPD4197	Approved
0.8026	Intermediate Similarity	NPD3617	Approved
0.8	Intermediate Similarity	NPD5329	Approved
0.7901	Intermediate Similarity	NPD6409	Approved
0.7901	Intermediate Similarity	NPD3618	Phase 1
0.7901	Intermediate Similarity	NPD5330	Approved
0.7901	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5205	Approved
0.7901	Intermediate Similarity	NPD7146	Approved
0.7901	Intermediate Similarity	NPD4688	Approved
0.7901	Intermediate Similarity	NPD4138	Approved
0.7901	Intermediate Similarity	NPD4690	Approved
0.7901	Intermediate Similarity	NPD4689	Approved
0.7901	Intermediate Similarity	NPD6684	Approved
0.7901	Intermediate Similarity	NPD5690	Phase 2
0.7901	Intermediate Similarity	NPD7334	Approved
0.7901	Intermediate Similarity	NPD7521	Approved
0.7901	Intermediate Similarity	NPD4693	Phase 3
0.7848	Intermediate Similarity	NPD3667	Approved
0.7821	Intermediate Similarity	NPD4695	Discontinued
0.7761	Intermediate Similarity	NPD287	Approved
0.7722	Intermediate Similarity	NPD8028	Phase 2
0.7711	Intermediate Similarity	NPD6672	Approved
0.7711	Intermediate Similarity	NPD6903	Approved
0.7711	Intermediate Similarity	NPD5737	Approved
0.7711	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5208	Approved
0.7692	Intermediate Similarity	NPD4195	Approved
0.7683	Intermediate Similarity	NPD5280	Approved
0.7683	Intermediate Similarity	NPD4694	Approved
0.7654	Intermediate Similarity	NPD4786	Approved
0.7654	Intermediate Similarity	NPD3668	Phase 3
0.7647	Intermediate Similarity	NPD6079	Approved
0.7619	Intermediate Similarity	NPD6080	Approved
0.7619	Intermediate Similarity	NPD4753	Phase 2
0.7619	Intermediate Similarity	NPD6673	Approved
0.7619	Intermediate Similarity	NPD5328	Approved
0.7619	Intermediate Similarity	NPD6904	Approved
0.747	Intermediate Similarity	NPD5279	Phase 3
0.747	Intermediate Similarity	NPD6098	Approved
0.747	Intermediate Similarity	NPD4519	Discontinued
0.747	Intermediate Similarity	NPD4623	Approved
0.7442	Intermediate Similarity	NPD5693	Phase 1
0.7386	Intermediate Similarity	NPD4629	Approved
0.7386	Intermediate Similarity	NPD5210	Approved
0.7381	Intermediate Similarity	NPD3573	Approved
0.7356	Intermediate Similarity	NPD4202	Approved
0.7326	Intermediate Similarity	NPD5207	Approved
0.7326	Intermediate Similarity	NPD5692	Phase 3
0.7303	Intermediate Similarity	NPD5222	Approved
0.7303	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD6001	Approved
0.7241	Intermediate Similarity	NPD5694	Approved
0.7241	Intermediate Similarity	NPD6050	Approved
0.7241	Intermediate Similarity	NPD5284	Approved
0.7241	Intermediate Similarity	NPD5281	Approved
0.7222	Intermediate Similarity	NPD5173	Approved
0.7191	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4096	Approved
0.7111	Intermediate Similarity	NPD4697	Phase 3
0.7108	Intermediate Similarity	NPD4788	Approved
0.7073	Intermediate Similarity	NPD4139	Approved
0.7073	Intermediate Similarity	NPD4692	Approved
0.7065	Intermediate Similarity	NPD5286	Approved
0.7065	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD4696	Approved
0.7033	Intermediate Similarity	NPD6083	Phase 2
0.7033	Intermediate Similarity	NPD6084	Phase 2
0.7033	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD5695	Phase 3
0.6989	Remote Similarity	NPD5223	Approved
0.6988	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5133	Approved
0.6966	Remote Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD5696	Approved
0.6915	Remote Similarity	NPD5225	Approved
0.6915	Remote Similarity	NPD5224	Approved
0.6915	Remote Similarity	NPD5091	Approved
0.6915	Remote Similarity	NPD5226	Approved
0.6915	Remote Similarity	NPD5211	Phase 2
0.6915	Remote Similarity	NPD4633	Approved
0.6897	Remote Similarity	NPD4518	Approved
0.6882	Remote Similarity	NPD4700	Approved
0.6854	Remote Similarity	NPD7515	Phase 2
0.6842	Remote Similarity	NPD5174	Approved
0.6842	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5654	Approved
0.6795	Remote Similarity	NPD4243	Approved
0.6771	Remote Similarity	NPD5141	Approved
0.6703	Remote Similarity	NPD7748	Approved
0.6703	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3495	Discontinued
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6633	Remote Similarity	NPD6614	Approved
0.6633	Remote Similarity	NPD5697	Approved
0.6625	Remote Similarity	NPD4784	Approved
0.6625	Remote Similarity	NPD4785	Approved
0.6579	Remote Similarity	NPD7331	Phase 2
0.6566	Remote Similarity	NPD6011	Approved
0.6566	Remote Similarity	NPD6881	Approved
0.6566	Remote Similarity	NPD4729	Approved
0.6566	Remote Similarity	NPD5168	Approved
0.6566	Remote Similarity	NPD4730	Approved
0.6566	Remote Similarity	NPD6899	Approved
0.6566	Remote Similarity	NPD5128	Approved
0.6559	Remote Similarity	NPD7732	Phase 3
0.6559	Remote Similarity	NPD7614	Phase 1
0.6552	Remote Similarity	NPD1694	Approved
0.6543	Remote Similarity	NPD7339	Approved
0.6543	Remote Similarity	NPD4190	Phase 3
0.6543	Remote Similarity	NPD6942	Approved
0.6543	Remote Similarity	NPD5275	Approved
0.6531	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD6675	Approved
0.6531	Remote Similarity	NPD6008	Approved
0.6531	Remote Similarity	NPD4768	Approved
0.6531	Remote Similarity	NPD5739	Approved
0.6531	Remote Similarity	NPD7128	Approved
0.6531	Remote Similarity	NPD4767	Approved
0.6526	Remote Similarity	NPD6404	Discontinued
0.65	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD6013	Approved
0.65	Remote Similarity	NPD6014	Approved
0.6489	Remote Similarity	NPD7902	Approved
0.6465	Remote Similarity	NPD5701	Approved
0.6465	Remote Similarity	NPD6412	Phase 2
0.6436	Remote Similarity	NPD7102	Approved
0.6436	Remote Similarity	NPD5250	Approved
0.6436	Remote Similarity	NPD6883	Approved
0.6436	Remote Similarity	NPD5135	Approved
0.6436	Remote Similarity	NPD5247	Approved
0.6436	Remote Similarity	NPD5251	Approved
0.6436	Remote Similarity	NPD4634	Approved
0.6436	Remote Similarity	NPD5169	Approved
0.6436	Remote Similarity	NPD5248	Approved
0.6436	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5249	Phase 3
0.6436	Remote Similarity	NPD7290	Approved
0.64	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD6650	Approved
0.6373	Remote Similarity	NPD6649	Approved
0.6373	Remote Similarity	NPD6869	Approved
0.6373	Remote Similarity	NPD6847	Approved
0.6373	Remote Similarity	NPD5127	Approved
0.6373	Remote Similarity	NPD6617	Approved
0.6373	Remote Similarity	NPD8130	Phase 1
0.6373	Remote Similarity	NPD5217	Approved
0.6373	Remote Similarity	NPD5216	Approved
0.6373	Remote Similarity	NPD5215	Approved
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6373	Approved
0.6337	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6882	Approved
0.6311	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5290	Discontinued
0.625	Remote Similarity	NPD6939	Phase 2
0.6237	Remote Similarity	NPD7631	Approved
0.6234	Remote Similarity	NPD7341	Phase 2
0.6234	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5360	Phase 3
0.6203	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5167	Approved
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.6163	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD7525	Registered
0.6154	Remote Similarity	NPD4224	Phase 2
0.6132	Remote Similarity	NPD6274	Approved
0.6132	Remote Similarity	NPD6868	Approved
0.6129	Remote Similarity	NPD7609	Phase 3
0.6125	Remote Similarity	NPD6923	Approved
0.6125	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6922	Approved
0.6125	Remote Similarity	NPD3698	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