NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	430.34
Volume:	479.716
LogP:	4.387
LogD:	4.62
LogS:	-5.031
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	5.197
Fsp3:	0.857
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:	-4.793
MDCK Permeability:	5.992215301375836e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.283
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	93.20511627197266%
Volume Distribution (VD):	1.272
Pgp-substrate:	3.4520368576049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.649
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.303
CYP3A4-substrate:	0.599

ADMET: Excretion

Clearance (CL):	6.268
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.439
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.035
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC477818

Natural Product ID:	NPC477818
*Common Name:**	17-[(3E)-5,6-dimethylhepta-3,6-dien-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,12,16-triol
IUPAC Name:	17-[(3E)-5,6-dimethylhepta-3,6-dien-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,12,16-triol
Synonyms:
Standard InCHIKey:	UPKVFBJFCYGFEP-BQYQJAHWSA-N
Standard InCHI:	InChI=1S/C28H46O3/c1-16(2)17(3)7-8-18(4)26-24(30)14-23-21-10-9-19-13-20(29)11-12-27(19,5)22(21)15-25(31)28(23,26)6/h7-8,17-26,29-31H,1,9-15H2,2-6H3/b8-7+
SMILES:	CC(/C=C/C(C)C(=C)C)C1C(CC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56657051
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO33580	Psammoclema sp.	Species	Chondropsidae	Eukaryota	n.a.	Nelson Bay, New South Wales, Australia (3243'0.5'' S, 15208'25.0'' E)	2006-OCT	PMID[19132863]

☑ 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
GI50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	7000	nM	PMID[19132863]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	17000	nM	PMID[19132863]
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	10000	nM	PMID[19132863]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	27000	nM	PMID[19132863]

☑ 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 NPC477818 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	175
0.1-0.2	1425
0.2-0.3	6381
0.3-0.4	16003
0.4-0.5	7358
0.5-0.6	4910
0.6-0.7	4530
0.7-0.8	1577
0.8-0.85	227
0.85-0.9	74
0.9-0.95	31
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC141941
0.9744	High Similarity	NPC193870
0.9744	High Similarity	NPC110778
0.962	High Similarity	NPC127606
0.962	High Similarity	NPC475798
0.9383	High Similarity	NPC6605
0.9383	High Similarity	NPC139724
0.9383	High Similarity	NPC24277
0.9383	High Similarity	NPC201273
0.9375	High Similarity	NPC124172
0.9375	High Similarity	NPC209802
0.9351	High Similarity	NPC477819
0.9351	High Similarity	NPC244385
0.9351	High Similarity	NPC6978
0.9351	High Similarity	NPC167037
0.9351	High Similarity	NPC138621
0.9351	High Similarity	NPC477817
0.9268	High Similarity	NPC474657
0.9268	High Similarity	NPC186145
0.9231	High Similarity	NPC80530
0.9231	High Similarity	NPC1319
0.9231	High Similarity	NPC273410
0.9157	High Similarity	NPC475664
0.9125	High Similarity	NPC470614
0.9125	High Similarity	NPC1272
0.9114	High Similarity	NPC236237
0.9114	High Similarity	NPC102253
0.9114	High Similarity	NPC26117
0.9114	High Similarity	NPC71535
0.9114	High Similarity	NPC322313
0.9114	High Similarity	NPC78545
0.9103	High Similarity	NPC285761
0.9091	High Similarity	NPC237460
0.9048	High Similarity	NPC105495
0.9048	High Similarity	NPC109744
0.9012	High Similarity	NPC113978
0.8987	High Similarity	NPC24504
0.8987	High Similarity	NPC472463
0.8961	High Similarity	NPC103822
0.8941	High Similarity	NPC475751
0.8941	High Similarity	NPC473956
0.8929	High Similarity	NPC470542
0.8902	High Similarity	NPC474493
0.8889	High Similarity	NPC218616
0.8889	High Similarity	NPC296701
0.8889	High Similarity	NPC248886
0.8875	High Similarity	NPC13554
0.8875	High Similarity	NPC47149
0.8861	High Similarity	NPC472500
0.8861	High Similarity	NPC85346
0.8861	High Similarity	NPC302041
0.8861	High Similarity	NPC472499
0.8861	High Similarity	NPC65897
0.8861	High Similarity	NPC87604
0.8861	High Similarity	NPC472502
0.8861	High Similarity	NPC475
0.8861	High Similarity	NPC477522
0.8846	High Similarity	NPC189883
0.8846	High Similarity	NPC134330
0.8846	High Similarity	NPC129165
0.8831	High Similarity	NPC472503
0.8831	High Similarity	NPC308440
0.8795	High Similarity	NPC318390
0.878	High Similarity	NPC207013
0.878	High Similarity	NPC232023
0.8765	High Similarity	NPC470383
0.875	High Similarity	NPC476316
0.8734	High Similarity	NPC471798
0.8734	High Similarity	NPC138502
0.8734	High Similarity	NPC214570
0.8734	High Similarity	NPC202540
0.8718	High Similarity	NPC257347
0.8718	High Similarity	NPC471723
0.8718	High Similarity	NPC141071
0.8718	High Similarity	NPC3403
0.8706	High Similarity	NPC133588
0.869	High Similarity	NPC269058
0.869	High Similarity	NPC299068
0.869	High Similarity	NPC261266
0.869	High Similarity	NPC71520
0.8675	High Similarity	NPC255882
0.8659	High Similarity	NPC50964
0.8659	High Similarity	NPC201852
0.8659	High Similarity	NPC20853
0.8642	High Similarity	NPC236112
0.8642	High Similarity	NPC475679
0.8625	High Similarity	NPC42853
0.8625	High Similarity	NPC148977
0.8625	High Similarity	NPC312328
0.8625	High Similarity	NPC275910
0.8625	High Similarity	NPC31828
0.8625	High Similarity	NPC477514
0.8608	High Similarity	NPC73875
0.8608	High Similarity	NPC321381
0.8608	High Similarity	NPC240604
0.8608	High Similarity	NPC107059
0.8608	High Similarity	NPC202642
0.8608	High Similarity	NPC14112
0.8608	High Similarity	NPC46160
0.8608	High Similarity	NPC470362
0.8608	High Similarity	NPC321016
0.8608	High Similarity	NPC38141
0.8608	High Similarity	NPC86305
0.8608	High Similarity	NPC300324
0.8608	High Similarity	NPC96319
0.8608	High Similarity	NPC113733
0.8605	High Similarity	NPC101886
0.8588	High Similarity	NPC271967
0.8571	High Similarity	NPC470360
0.8571	High Similarity	NPC111234
0.8554	High Similarity	NPC470558
0.8554	High Similarity	NPC82623
0.8554	High Similarity	NPC134481
0.8537	High Similarity	NPC474531
0.8537	High Similarity	NPC476646
0.8537	High Similarity	NPC23852
0.8537	High Similarity	NPC209620
0.8519	High Similarity	NPC472742
0.8519	High Similarity	NPC80297
0.8519	High Similarity	NPC30986
0.8519	High Similarity	NPC209430
0.8519	High Similarity	NPC49627
0.8519	High Similarity	NPC49599
0.8519	High Similarity	NPC116119
0.8519	High Similarity	NPC475727
0.8506	High Similarity	NPC3345
0.8506	High Similarity	NPC291484
0.8506	High Similarity	NPC11216
0.8506	High Similarity	NPC329596
0.8506	High Similarity	NPC204188
0.8506	High Similarity	NPC80561
0.85	High Similarity	NPC260301
0.85	High Similarity	NPC307336
0.85	High Similarity	NPC130136
0.85	High Similarity	NPC155986
0.85	High Similarity	NPC318495
0.85	High Similarity	NPC198968
0.8488	Intermediate Similarity	NPC193360
0.8488	Intermediate Similarity	NPC4574
0.8488	Intermediate Similarity	NPC212596
0.8488	Intermediate Similarity	NPC2158
0.8488	Intermediate Similarity	NPC471952
0.8481	Intermediate Similarity	NPC162742
0.8481	Intermediate Similarity	NPC104387
0.8481	Intermediate Similarity	NPC240235
0.8481	Intermediate Similarity	NPC230704
0.8481	Intermediate Similarity	NPC322353
0.8481	Intermediate Similarity	NPC134847
0.8481	Intermediate Similarity	NPC22105
0.8481	Intermediate Similarity	NPC230301
0.8481	Intermediate Similarity	NPC178383
0.8481	Intermediate Similarity	NPC136188
0.8481	Intermediate Similarity	NPC304309
0.8481	Intermediate Similarity	NPC285893
0.8481	Intermediate Similarity	NPC118508
0.8481	Intermediate Similarity	NPC28657
0.8481	Intermediate Similarity	NPC185536
0.8481	Intermediate Similarity	NPC70982
0.8481	Intermediate Similarity	NPC121744
0.8481	Intermediate Similarity	NPC288035
0.8481	Intermediate Similarity	NPC291503
0.8481	Intermediate Similarity	NPC212879
0.8481	Intermediate Similarity	NPC231256
0.8471	Intermediate Similarity	NPC6391
0.8471	Intermediate Similarity	NPC94462
0.8471	Intermediate Similarity	NPC152808
0.8471	Intermediate Similarity	NPC293287
0.8471	Intermediate Similarity	NPC121981
0.8462	Intermediate Similarity	NPC182717
0.8462	Intermediate Similarity	NPC474140
0.8452	Intermediate Similarity	NPC470077
0.8452	Intermediate Similarity	NPC256567
0.8452	Intermediate Similarity	NPC478102
0.8444	Intermediate Similarity	NPC253115
0.8444	Intermediate Similarity	NPC304899
0.8442	Intermediate Similarity	NPC45296
0.8434	Intermediate Similarity	NPC470049
0.8434	Intermediate Similarity	NPC30166
0.8434	Intermediate Similarity	NPC49964
0.8434	Intermediate Similarity	NPC87489
0.8427	Intermediate Similarity	NPC111015
0.8415	Intermediate Similarity	NPC287749
0.8415	Intermediate Similarity	NPC96362
0.8415	Intermediate Similarity	NPC234193
0.8415	Intermediate Similarity	NPC241290
0.8415	Intermediate Similarity	NPC164840
0.8415	Intermediate Similarity	NPC209944
0.8409	Intermediate Similarity	NPC41554
0.8409	Intermediate Similarity	NPC97404
0.8395	Intermediate Similarity	NPC473943
0.8395	Intermediate Similarity	NPC11908
0.8395	Intermediate Similarity	NPC186191
0.8395	Intermediate Similarity	NPC76931
0.8395	Intermediate Similarity	NPC474216
0.8395	Intermediate Similarity	NPC307965
0.8395	Intermediate Similarity	NPC18603
0.8395	Intermediate Similarity	NPC472501
0.8395	Intermediate Similarity	NPC205455
0.8395	Intermediate Similarity	NPC301707
0.8395	Intermediate Similarity	NPC300499

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 NPC477818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1630
0.2-0.3	4466
0.3-0.4	2066
0.4-0.5	382
0.5-0.6	159
0.6-0.7	168
0.7-0.8	106
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9114	High Similarity	NPD7525	Registered
0.8608	High Similarity	NPD3701	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7339	Approved
0.8481	Intermediate Similarity	NPD6942	Approved
0.8161	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4784	Approved
0.8125	Intermediate Similarity	NPD4785	Approved
0.8101	Intermediate Similarity	NPD4243	Approved
0.8072	Intermediate Similarity	NPD7645	Phase 2
0.7912	Intermediate Similarity	NPD4202	Approved
0.7901	Intermediate Similarity	NPD6926	Approved
0.7901	Intermediate Similarity	NPD6924	Approved
0.7875	Intermediate Similarity	NPD7152	Approved
0.7875	Intermediate Similarity	NPD7150	Approved
0.7875	Intermediate Similarity	NPD7151	Approved
0.7857	Intermediate Similarity	NPD6929	Approved
0.7831	Intermediate Similarity	NPD6932	Approved
0.7816	Intermediate Similarity	NPD4786	Approved
0.7802	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7765	Intermediate Similarity	NPD6930	Phase 2
0.7765	Intermediate Similarity	NPD6931	Approved
0.7765	Intermediate Similarity	NPD4748	Discontinued
0.775	Intermediate Similarity	NPD7144	Approved
0.775	Intermediate Similarity	NPD7143	Approved
0.7738	Intermediate Similarity	NPD7145	Approved
0.7711	Intermediate Similarity	NPD6933	Approved
0.7684	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD4195	Approved
0.764	Intermediate Similarity	NPD3618	Phase 1
0.7625	Intermediate Similarity	NPD6923	Approved
0.7625	Intermediate Similarity	NPD6922	Approved
0.7619	Intermediate Similarity	NPD5776	Phase 2
0.7619	Intermediate Similarity	NPD6925	Approved
0.7614	Intermediate Similarity	NPD3133	Approved
0.7614	Intermediate Similarity	NPD3666	Approved
0.7614	Intermediate Similarity	NPD3665	Phase 1
0.7614	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7639	Approved
0.7604	Intermediate Similarity	NPD5285	Approved
0.7604	Intermediate Similarity	NPD5286	Approved
0.7604	Intermediate Similarity	NPD7640	Approved
0.7604	Intermediate Similarity	NPD4696	Approved
0.759	Intermediate Similarity	NPD4190	Phase 3
0.759	Intermediate Similarity	NPD5275	Approved
0.7586	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD4755	Approved
0.7558	Intermediate Similarity	NPD7514	Phase 3
0.7558	Intermediate Similarity	NPD7509	Discontinued
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6695	Phase 3
0.7471	Intermediate Similarity	NPD6902	Approved
0.7449	Intermediate Similarity	NPD5224	Approved
0.7449	Intermediate Similarity	NPD5211	Phase 2
0.7449	Intermediate Similarity	NPD4633	Approved
0.7449	Intermediate Similarity	NPD5225	Approved
0.7449	Intermediate Similarity	NPD5226	Approved
0.7442	Intermediate Similarity	NPD6683	Phase 2
0.7423	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD5174	Approved
0.7374	Intermediate Similarity	NPD5175	Approved
0.7356	Intermediate Similarity	NPD7332	Phase 2
0.7333	Intermediate Similarity	NPD6893	Approved
0.7317	Intermediate Similarity	NPD4787	Phase 1
0.7303	Intermediate Similarity	NPD4788	Approved
0.73	Intermediate Similarity	NPD5141	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4634	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7204	Intermediate Similarity	NPD4753	Phase 2
0.72	Intermediate Similarity	NPD4754	Approved
0.7195	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD7524	Approved
0.7174	Intermediate Similarity	NPD7750	Discontinued
0.7159	Intermediate Similarity	NPD6928	Phase 2
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7157	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.7126	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7113	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD6011	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7087	Intermediate Similarity	NPD4730	Approved
0.7087	Intermediate Similarity	NPD4729	Approved
0.7079	Intermediate Similarity	NPD6898	Phase 1
0.7075	Intermediate Similarity	NPD4632	Approved
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD4767	Approved
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD7515	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.7033	Intermediate Similarity	NPD4197	Approved
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.7019	Intermediate Similarity	NPD6012	Approved
0.7019	Intermediate Similarity	NPD6013	Approved
0.7019	Intermediate Similarity	NPD6014	Approved
0.701	Intermediate Similarity	NPD5210	Approved
0.701	Intermediate Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5701	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD8264	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.697	Remote Similarity	NPD5290	Discontinued
0.6952	Remote Similarity	NPD5251	Approved
0.6952	Remote Similarity	NPD5169	Approved
0.6952	Remote Similarity	NPD5250	Approved
0.6952	Remote Similarity	NPD5248	Approved
0.6952	Remote Similarity	NPD5249	Phase 3
0.6952	Remote Similarity	NPD5247	Approved
0.6952	Remote Similarity	NPD5135	Approved
0.6952	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6114	Approved
0.6932	Remote Similarity	NPD6697	Approved
0.6932	Remote Similarity	NPD6118	Approved
0.6932	Remote Similarity	NPD6115	Approved
0.6931	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD5128	Approved
0.6915	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7516	Approved
0.6887	Remote Similarity	NPD5215	Approved
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5217	Approved
0.6887	Remote Similarity	NPD5127	Approved
0.6887	Remote Similarity	NPD5216	Approved
0.6882	Remote Similarity	NPD6684	Approved
0.6882	Remote Similarity	NPD4693	Phase 3
0.6882	Remote Similarity	NPD7521	Approved
0.6882	Remote Similarity	NPD4138	Approved
0.6882	Remote Similarity	NPD5330	Approved
0.6882	Remote Similarity	NPD4689	Approved
0.6882	Remote Similarity	NPD7146	Approved
0.6882	Remote Similarity	NPD5690	Phase 2
0.6882	Remote Similarity	NPD5279	Phase 3
0.6882	Remote Similarity	NPD4688	Approved
0.6882	Remote Similarity	NPD6409	Approved
0.6882	Remote Similarity	NPD7334	Approved
0.6882	Remote Similarity	NPD5205	Approved
0.6882	Remote Similarity	NPD4690	Approved
0.6881	Remote Similarity	NPD6009	Approved
0.6875	Remote Similarity	NPD7087	Discontinued
0.6869	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD6084	Phase 2
0.6848	Remote Similarity	NPD3668	Phase 3
0.6847	Remote Similarity	NPD6054	Approved
0.6847	Remote Similarity	NPD8294	Approved
0.6847	Remote Similarity	NPD8377	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6827	Remote Similarity	NPD6412	Phase 2
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6116	Phase 1
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD8033	Approved
0.6782	Remote Similarity	NPD3703	Phase 2
0.6737	Remote Similarity	NPD6903	Approved
0.6737	Remote Similarity	NPD4722	Approved
0.6737	Remote Similarity	NPD4723	Approved
0.6735	Remote Similarity	NPD7748	Approved
0.6731	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD6370	Approved
0.6706	Remote Similarity	NPD4244	Approved
0.6706	Remote Similarity	NPD4245	Approved
0.6705	Remote Similarity	NPD6117	Approved
0.6702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5280	Approved
0.6702	Remote Similarity	NPD4694	Approved
0.6701	Remote Similarity	NPD7637	Suspended
0.6701	Remote Similarity	NPD5284	Approved
0.6701	Remote Similarity	NPD5281	Approved
0.67	Remote Similarity	NPD7902	Approved
0.6697	Remote Similarity	NPD5167	Approved
0.6696	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD6319	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