NPASS Compound

Structure

NPC103822 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 15 1 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 1 0 0 0 15 21 1 1 0 0 0 16 23 1 1 0 0 0 17 6 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 1 0 0 0 19 21 1 1 0 0 0 20 2 1 1 0 0 0 21 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.26
Volume:	352.49
LogP:	4.376
LogD:	4.451
LogS:	-4.088
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	4.505
Fsp3:	0.905
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:	-4.652
MDCK Permeability:	2.305323869222775e-05
Pgp-inhibitor:	0.4
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.465
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	92.68905639648438%
Volume Distribution (VD):	0.831
Pgp-substrate:	4.047845840454102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.354
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.537
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	7.636
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.229
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.971
Carcinogencity:	0.244
Eye Corrosion:	0.985
Eye Irritation:	0.962
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC103822

Natural Product ID:	NPC103822
*Common Name:**	Stereonsteroid A
IUPAC Name:	(3S,5S,8S,9S,10R,13R,14S,17R)-17-ethenyl-10-(hydroxymethyl)-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	VBJNSFFFEBGPIC-YVFDZHEOSA-N
Standard InCHI:	InChI=1S/C21H34O2/c1-3-14-5-7-18-17-6-4-15-12-16(23)8-11-21(15,13-22)19(17)9-10-20(14,18)2/h3,14-19,22-23H,1,4-13H2,2H3/t14-,15-,16-,17-,18-,19-,20+,21+/m0/s1
SMILES:	C=C[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(CO)CC[C@@H](C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491368
PubChem CID:	11702475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins 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
NPO33076	stereonephthya crystalliana	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16441077]

☑ 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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	7.5	ug ml-1	PMID[523099]
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.5	ug.mL-1	PMID[523099]

☑ 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 NPC103822 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	145
0.1-0.2	1835
0.2-0.3	9449
0.3-0.4	14987
0.4-0.5	6269
0.5-0.6	4991
0.6-0.7	3651
0.7-0.8	1102
0.8-0.85	164
0.85-0.9	94
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC472503
0.9296	High Similarity	NPC308440
0.9178	High Similarity	NPC202540
0.9054	High Similarity	NPC477819
0.9054	High Similarity	NPC31828
0.9054	High Similarity	NPC477817
0.9014	High Similarity	NPC111234
0.8961	High Similarity	NPC477818
0.8961	High Similarity	NPC141941
0.8961	High Similarity	NPC193870
0.8933	High Similarity	NPC80297
0.8933	High Similarity	NPC472742
0.8933	High Similarity	NPC116119
0.8933	High Similarity	NPC475727
0.8904	High Similarity	NPC185536
0.8904	High Similarity	NPC70982
0.8904	High Similarity	NPC230704
0.8904	High Similarity	NPC3403
0.8904	High Similarity	NPC212879
0.8904	High Similarity	NPC104387
0.8904	High Similarity	NPC240235
0.8904	High Similarity	NPC231256
0.8904	High Similarity	NPC178383
0.8889	High Similarity	NPC195489
0.8873	High Similarity	NPC45296
0.8846	High Similarity	NPC475798
0.8846	High Similarity	NPC127606
0.8816	High Similarity	NPC71535
0.8816	High Similarity	NPC78545
0.8816	High Similarity	NPC475679
0.88	High Similarity	NPC472500
0.88	High Similarity	NPC87604
0.88	High Similarity	NPC167037
0.88	High Similarity	NPC138621
0.88	High Similarity	NPC244385
0.88	High Similarity	NPC472499
0.88	High Similarity	NPC6978
0.88	High Similarity	NPC285761
0.8784	High Similarity	NPC14112
0.8784	High Similarity	NPC237460
0.8784	High Similarity	NPC78067
0.8784	High Similarity	NPC134330
0.8784	High Similarity	NPC129165
0.8784	High Similarity	NPC91573
0.8784	High Similarity	NPC278091
0.8784	High Similarity	NPC86305
0.8784	High Similarity	NPC93662
0.8767	High Similarity	NPC5046
0.8767	High Similarity	NPC145552
0.8767	High Similarity	NPC254509
0.8767	High Similarity	NPC25511
0.8767	High Similarity	NPC192638
0.8767	High Similarity	NPC62657
0.8767	High Similarity	NPC49168
0.8767	High Similarity	NPC196358
0.8732	High Similarity	NPC210323
0.8718	High Similarity	NPC110778
0.8718	High Similarity	NPC113978
0.8684	High Similarity	NPC80530
0.8684	High Similarity	NPC24504
0.8684	High Similarity	NPC472463
0.8684	High Similarity	NPC476316
0.8684	High Similarity	NPC273410
0.8667	High Similarity	NPC257191
0.8667	High Similarity	NPC212241
0.8667	High Similarity	NPC119355
0.8667	High Similarity	NPC248830
0.8667	High Similarity	NPC331618
0.8649	High Similarity	NPC141071
0.8649	High Similarity	NPC200243
0.8649	High Similarity	NPC471723
0.8649	High Similarity	NPC257347
0.8625	High Similarity	NPC139724
0.8625	High Similarity	NPC6605
0.8608	High Similarity	NPC474493
0.8608	High Similarity	NPC209802
0.8592	High Similarity	NPC2648
0.859	High Similarity	NPC248886
0.859	High Similarity	NPC296701
0.859	High Similarity	NPC50964
0.859	High Similarity	NPC218616
0.8571	High Similarity	NPC102253
0.8571	High Similarity	NPC236237
0.8571	High Similarity	NPC47149
0.8571	High Similarity	NPC26117
0.8571	High Similarity	NPC322313
0.8571	High Similarity	NPC13554
0.8553	High Similarity	NPC302041
0.8553	High Similarity	NPC85346
0.8553	High Similarity	NPC472342
0.8553	High Similarity	NPC475
0.8553	High Similarity	NPC472502
0.8553	High Similarity	NPC42853
0.8553	High Similarity	NPC301707
0.8553	High Similarity	NPC65897
0.8553	High Similarity	NPC102708
0.8553	High Similarity	NPC148977
0.8533	High Similarity	NPC38141
0.8533	High Similarity	NPC321381
0.8533	High Similarity	NPC321016
0.8533	High Similarity	NPC470362
0.8533	High Similarity	NPC113733
0.8533	High Similarity	NPC107059
0.8533	High Similarity	NPC189883
0.8519	High Similarity	NPC474657
0.8519	High Similarity	NPC186145
0.8514	High Similarity	NPC476736
0.85	High Similarity	NPC470360
0.8481	Intermediate Similarity	NPC211135
0.8481	Intermediate Similarity	NPC216420
0.8481	Intermediate Similarity	NPC470929
0.8481	Intermediate Similarity	NPC232023
0.8481	Intermediate Similarity	NPC85095
0.8481	Intermediate Similarity	NPC134481
0.8481	Intermediate Similarity	NPC470558
0.8481	Intermediate Similarity	NPC82623
0.8462	Intermediate Similarity	NPC470383
0.8462	Intermediate Similarity	NPC209620
0.8462	Intermediate Similarity	NPC23852
0.8442	Intermediate Similarity	NPC1319
0.8442	Intermediate Similarity	NPC30986
0.8442	Intermediate Similarity	NPC209430
0.8442	Intermediate Similarity	NPC49599
0.8442	Intermediate Similarity	NPC49627
0.8429	Intermediate Similarity	NPC27243
0.8429	Intermediate Similarity	NPC476737
0.8421	Intermediate Similarity	NPC138502
0.8421	Intermediate Similarity	NPC260301
0.8421	Intermediate Similarity	NPC198968
0.8421	Intermediate Similarity	NPC214570
0.8421	Intermediate Similarity	NPC318495
0.8421	Intermediate Similarity	NPC307336
0.8421	Intermediate Similarity	NPC471798
0.8421	Intermediate Similarity	NPC155986
0.8415	Intermediate Similarity	NPC475664
0.8406	Intermediate Similarity	NPC114891
0.84	Intermediate Similarity	NPC230301
0.84	Intermediate Similarity	NPC285893
0.84	Intermediate Similarity	NPC28657
0.84	Intermediate Similarity	NPC136188
0.84	Intermediate Similarity	NPC304309
0.84	Intermediate Similarity	NPC22105
0.84	Intermediate Similarity	NPC162742
0.84	Intermediate Similarity	NPC288035
0.84	Intermediate Similarity	NPC134847
0.8395	Intermediate Similarity	NPC201273
0.8395	Intermediate Similarity	NPC261266
0.8395	Intermediate Similarity	NPC24277
0.8395	Intermediate Similarity	NPC299068
0.8395	Intermediate Similarity	NPC71520
0.8395	Intermediate Similarity	NPC269058
0.8378	Intermediate Similarity	NPC472506
0.8375	Intermediate Similarity	NPC86238
0.8375	Intermediate Similarity	NPC255882
0.8375	Intermediate Similarity	NPC124172
0.8354	Intermediate Similarity	NPC1272
0.8354	Intermediate Similarity	NPC470614
0.8354	Intermediate Similarity	NPC472504
0.8333	Intermediate Similarity	NPC241290
0.8333	Intermediate Similarity	NPC164840
0.8333	Intermediate Similarity	NPC236112
0.8333	Intermediate Similarity	NPC234193
0.8333	Intermediate Similarity	NPC209944
0.8313	Intermediate Similarity	NPC74258
0.8313	Intermediate Similarity	NPC109744
0.8312	Intermediate Similarity	NPC11908
0.8312	Intermediate Similarity	NPC275910
0.8312	Intermediate Similarity	NPC76931
0.8312	Intermediate Similarity	NPC472501
0.8312	Intermediate Similarity	NPC474216
0.8312	Intermediate Similarity	NPC312328
0.8312	Intermediate Similarity	NPC307965
0.8312	Intermediate Similarity	NPC477522
0.8312	Intermediate Similarity	NPC18603
0.8312	Intermediate Similarity	NPC473943
0.8289	Intermediate Similarity	NPC300324
0.8289	Intermediate Similarity	NPC73875
0.8289	Intermediate Similarity	NPC240604
0.8289	Intermediate Similarity	NPC63958
0.8289	Intermediate Similarity	NPC202642
0.8289	Intermediate Similarity	NPC46160
0.8272	Intermediate Similarity	NPC22133
0.8261	Intermediate Similarity	NPC71460
0.8261	Intermediate Similarity	NPC148174
0.8261	Intermediate Similarity	NPC218585
0.825	Intermediate Similarity	NPC207013
0.8243	Intermediate Similarity	NPC164045
0.8228	Intermediate Similarity	NPC264245
0.8228	Intermediate Similarity	NPC47761
0.8228	Intermediate Similarity	NPC474531
0.8219	Intermediate Similarity	NPC477820
0.8219	Intermediate Similarity	NPC66407
0.8219	Intermediate Similarity	NPC254037
0.8219	Intermediate Similarity	NPC9942
0.8219	Intermediate Similarity	NPC129829
0.8214	Intermediate Similarity	NPC475751
0.8214	Intermediate Similarity	NPC473956
0.8205	Intermediate Similarity	NPC328714
0.8205	Intermediate Similarity	NPC28862
0.8205	Intermediate Similarity	NPC84694

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 NPC103822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	2205
0.2-0.3	4488
0.3-0.4	1637
0.4-0.5	280
0.5-0.6	174
0.6-0.7	153
0.7-0.8	70
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7525	Registered
0.84	Intermediate Similarity	NPD7339	Approved
0.84	Intermediate Similarity	NPD6942	Approved
0.8052	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6924	Approved
0.7792	Intermediate Similarity	NPD6926	Approved
0.7763	Intermediate Similarity	NPD7150	Approved
0.7763	Intermediate Similarity	NPD7152	Approved
0.7763	Intermediate Similarity	NPD7151	Approved
0.775	Intermediate Similarity	NPD6929	Approved
0.775	Intermediate Similarity	NPD7645	Phase 2
0.7733	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6932	Approved
0.7711	Intermediate Similarity	NPD4786	Approved
0.7654	Intermediate Similarity	NPD6931	Approved
0.7654	Intermediate Similarity	NPD6930	Phase 2
0.7647	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4787	Phase 1
0.7632	Intermediate Similarity	NPD7143	Approved
0.7632	Intermediate Similarity	NPD7144	Approved
0.7625	Intermediate Similarity	NPD7145	Approved
0.7595	Intermediate Similarity	NPD6933	Approved
0.7564	Intermediate Similarity	NPD4785	Approved
0.7564	Intermediate Similarity	NPD4784	Approved
0.7532	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4243	Approved
0.7532	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6925	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD6922	Approved
0.75	Intermediate Similarity	NPD5776	Phase 2
0.75	Intermediate Similarity	NPD6923	Approved
0.7471	Intermediate Similarity	NPD5328	Approved
0.747	Intermediate Similarity	NPD3667	Approved
0.7439	Intermediate Similarity	NPD7514	Phase 3
0.7407	Intermediate Similarity	NPD6118	Approved
0.7407	Intermediate Similarity	NPD6115	Approved
0.7407	Intermediate Similarity	NPD6114	Approved
0.7407	Intermediate Similarity	NPD6697	Approved
0.7381	Intermediate Similarity	NPD4788	Approved
0.7381	Intermediate Similarity	NPD6695	Phase 3
0.7349	Intermediate Similarity	NPD6902	Approved
0.7342	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3618	Phase 1
0.7317	Intermediate Similarity	NPD6683	Phase 2
0.7294	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3703	Phase 2
0.7229	Intermediate Similarity	NPD7509	Discontinued
0.7229	Intermediate Similarity	NPD4748	Discontinued
0.7229	Intermediate Similarity	NPD7332	Phase 2
0.7229	Intermediate Similarity	NPD6928	Phase 2
0.7209	Intermediate Similarity	NPD6893	Approved
0.7204	Intermediate Similarity	NPD7638	Approved
0.716	Intermediate Similarity	NPD6117	Approved
0.7128	Intermediate Similarity	NPD7640	Approved
0.7128	Intermediate Similarity	NPD7639	Approved
0.7111	Intermediate Similarity	NPD8035	Phase 2
0.7111	Intermediate Similarity	NPD8034	Phase 2
0.7108	Intermediate Similarity	NPD4195	Approved
0.7093	Intermediate Similarity	NPD3666	Approved
0.7093	Intermediate Similarity	NPD3133	Approved
0.7093	Intermediate Similarity	NPD3665	Phase 1
0.7073	Intermediate Similarity	NPD6116	Phase 1
0.7045	Intermediate Similarity	NPD7750	Discontinued
0.7045	Intermediate Similarity	NPD7524	Approved
0.7037	Intermediate Similarity	NPD5275	Approved
0.7037	Intermediate Similarity	NPD4190	Phase 3
0.7033	Intermediate Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD5221	Approved
0.6989	Remote Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4789	Approved
0.6962	Remote Similarity	NPD4245	Approved
0.6962	Remote Similarity	NPD4244	Approved
0.6941	Remote Similarity	NPD6898	Phase 1
0.6923	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5360	Phase 3
0.6915	Remote Similarity	NPD5173	Approved
0.6848	Remote Similarity	NPD6399	Phase 3
0.6835	Remote Similarity	NPD3698	Phase 2
0.6829	Remote Similarity	NPD8264	Approved
0.6809	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5286	Approved
0.6771	Remote Similarity	NPD4696	Approved
0.6771	Remote Similarity	NPD5285	Approved
0.6753	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5279	Phase 3
0.6739	Remote Similarity	NPD7515	Phase 2
0.6739	Remote Similarity	NPD7087	Discontinued
0.6737	Remote Similarity	NPD4755	Approved
0.6705	Remote Similarity	NPD3668	Phase 3
0.6703	Remote Similarity	NPD4753	Phase 2
0.6701	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6633	Remote Similarity	NPD5226	Approved
0.6633	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD4633	Approved
0.6629	Remote Similarity	NPD5329	Approved
0.6598	Remote Similarity	NPD4700	Approved
0.6588	Remote Similarity	NPD3671	Phase 1
0.6566	Remote Similarity	NPD5175	Approved
0.6566	Remote Similarity	NPD5174	Approved
0.6559	Remote Similarity	NPD7637	Suspended
0.6526	Remote Similarity	NPD5210	Approved
0.6526	Remote Similarity	NPD4629	Approved
0.6517	Remote Similarity	NPD4197	Approved
0.6505	Remote Similarity	NPD4634	Approved
0.65	Remote Similarity	NPD6705	Phase 1
0.65	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6465	Remote Similarity	NPD7632	Discontinued
0.6463	Remote Similarity	NPD4758	Discontinued
0.6452	Remote Similarity	NPD6700	Approved
0.6452	Remote Similarity	NPD7136	Phase 2
0.6452	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6675	Approved
0.6436	Remote Similarity	NPD5739	Approved
0.6436	Remote Similarity	NPD7128	Approved
0.6436	Remote Similarity	NPD6402	Approved
0.6421	Remote Similarity	NPD7748	Approved
0.6413	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4754	Approved
0.6392	Remote Similarity	NPD6083	Phase 2
0.6392	Remote Similarity	NPD6084	Phase 2
0.6383	Remote Similarity	NPD6702	Approved
0.6383	Remote Similarity	NPD6703	Approved
0.6374	Remote Similarity	NPD7146	Approved
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD7521	Approved
0.6374	Remote Similarity	NPD5330	Approved
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD7334	Approved
0.6374	Remote Similarity	NPD6684	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6374	Remote Similarity	NPD5690	Phase 2
0.6374	Remote Similarity	NPD6409	Approved
0.6373	Remote Similarity	NPD5697	Approved
0.6346	Remote Similarity	NPD7290	Approved
0.6346	Remote Similarity	NPD7102	Approved
0.6346	Remote Similarity	NPD6883	Approved
0.6344	Remote Similarity	NPD6051	Approved
0.6321	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD8171	Discontinued
0.6311	Remote Similarity	NPD5168	Approved
0.6311	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD4730	Approved
0.6311	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD6649	Approved
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD8130	Phase 1
0.6275	Remote Similarity	NPD4768	Approved
0.6275	Remote Similarity	NPD4767	Approved
0.6265	Remote Similarity	NPD6081	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD4224	Phase 2
0.625	Remote Similarity	NPD6013	Approved
0.6239	Remote Similarity	NPD7327	Approved
0.6239	Remote Similarity	NPD7328	Approved
0.6237	Remote Similarity	NPD6903	Approved
0.6237	Remote Similarity	NPD4722	Approved
0.6237	Remote Similarity	NPD4723	Approved
0.6237	Remote Similarity	NPD5737	Approved
0.6237	Remote Similarity	NPD6672	Approved
0.6226	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD6882	Approved
0.6224	Remote Similarity	NPD7902	Approved
0.6214	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD5701	Approved
0.6207	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5364	Discontinued
0.6207	Remote Similarity	NPD3617	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.6196	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4694	Approved
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5247	Approved
0.619	Remote Similarity	NPD5248	Approved
0.619	Remote Similarity	NPD5249	Phase 3

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