NPASS Compound

Structure

NPC472484 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 -1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 -0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 -1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 -0.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 1.0520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2471 -0.0187 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 0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3996 1.8955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0423 -2.3790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 6 0 0 0 14 17 1 1 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 2 1 6 0 0 0 18 3 1 1 0 0 0 19 9 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	2.128
LogD:	1.516
LogS:	-3.498
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	6.085
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.688
MDCK Permeability:	2.268613752676174e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.818
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	81.8726806640625%
Volume Distribution (VD):	1.505
Pgp-substrate:	16.15689468383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	4.11
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.579
Maximum Recommended Daily Dose:	0.178
Skin Sensitization:	0.034
Carcinogencity:	0.626
Eye Corrosion:	0.189
Eye Irritation:	0.192
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC472484

Natural Product ID:	NPC472484
*Common Name:**	PYLFLALBRCJWJW-ZLARMEDBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PYLFLALBRCJWJW-ZLARMEDBSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-16(22)19-9-5-14-17(2,12-21)7-4-8-18(14,3)15(19)6-10-20(13,23)11-19/h6,13-14,21,23H,4-5,7-12H2,1-3H3/t13-,14+,17-,18+,19+,20-/m0/s1
SMILES:	OC[C@]1(C)CCC[C@@]2([C@@H]1CC[C@]13C2=CC[C@](C1)([C@H](C3=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426492
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ 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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[479359]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[479359]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[479359]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[479359]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[479359]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[479359]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[479359]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[479359]

☑ 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 NPC472484 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	167
0.1-0.2	1255
0.2-0.3	6087
0.3-0.4	15439
0.4-0.5	7092
0.5-0.6	6324
0.6-0.7	4494
0.7-0.8	1637
0.8-0.85	127
0.85-0.9	61
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472482
1.0	High Similarity	NPC472481
0.9639	High Similarity	NPC472483
0.963	High Similarity	NPC472480
0.9405	High Similarity	NPC328313
0.9398	High Similarity	NPC472491
0.9398	High Similarity	NPC472494
0.9294	High Similarity	NPC472475
0.9294	High Similarity	NPC472477
0.9205	High Similarity	NPC472485
0.907	High Similarity	NPC76879
0.9059	High Similarity	NPC472493
0.9048	High Similarity	NPC474218
0.9036	High Similarity	NPC472492
0.8966	High Similarity	NPC472476
0.8953	High Similarity	NPC53911
0.8941	High Similarity	NPC472479
0.8929	High Similarity	NPC59453
0.8929	High Similarity	NPC221758
0.8929	High Similarity	NPC82902
0.8916	High Similarity	NPC151519
0.8851	High Similarity	NPC472489
0.8721	High Similarity	NPC145879
0.8721	High Similarity	NPC469994
0.8721	High Similarity	NPC20688
0.8721	High Similarity	NPC474778
0.8721	High Similarity	NPC474733
0.8721	High Similarity	NPC31564
0.8721	High Similarity	NPC474732
0.8721	High Similarity	NPC51014
0.8706	High Similarity	NPC329043
0.8706	High Similarity	NPC58841
0.8706	High Similarity	NPC321187
0.8706	High Similarity	NPC161423
0.8706	High Similarity	NPC227064
0.869	High Similarity	NPC193347
0.8636	High Similarity	NPC310010
0.8636	High Similarity	NPC326627
0.8636	High Similarity	NPC2983
0.8636	High Similarity	NPC32830
0.8636	High Similarity	NPC477943
0.8636	High Similarity	NPC474245
0.8621	High Similarity	NPC475740
0.8621	High Similarity	NPC96496
0.8621	High Similarity	NPC317590
0.8621	High Similarity	NPC58063
0.8605	High Similarity	NPC469948
0.8571	High Similarity	NPC14151
0.8571	High Similarity	NPC469599
0.8556	High Similarity	NPC474807
0.8556	High Similarity	NPC233118
0.8539	High Similarity	NPC320026
0.8539	High Similarity	NPC171441
0.8506	High Similarity	NPC155011
0.8506	High Similarity	NPC472488
0.8488	Intermediate Similarity	NPC237712
0.8488	Intermediate Similarity	NPC144258
0.8488	Intermediate Similarity	NPC214043
0.8488	Intermediate Similarity	NPC85774
0.8452	Intermediate Similarity	NPC472478
0.8444	Intermediate Similarity	NPC154101
0.8427	Intermediate Similarity	NPC268406
0.8427	Intermediate Similarity	NPC1015
0.8427	Intermediate Similarity	NPC31985
0.8427	Intermediate Similarity	NPC119416
0.8427	Intermediate Similarity	NPC472971
0.8427	Intermediate Similarity	NPC26959
0.8427	Intermediate Similarity	NPC472970
0.8427	Intermediate Similarity	NPC186688
0.8427	Intermediate Similarity	NPC476733
0.8427	Intermediate Similarity	NPC215029
0.8409	Intermediate Similarity	NPC90652
0.8404	Intermediate Similarity	NPC110149
0.8391	Intermediate Similarity	NPC471224
0.8372	Intermediate Similarity	NPC477852
0.8372	Intermediate Similarity	NPC278648
0.8372	Intermediate Similarity	NPC476082
0.837	Intermediate Similarity	NPC263347
0.8352	Intermediate Similarity	NPC470375
0.8352	Intermediate Similarity	NPC470376
0.8333	Intermediate Similarity	NPC69622
0.8333	Intermediate Similarity	NPC474113
0.8333	Intermediate Similarity	NPC48010
0.8333	Intermediate Similarity	NPC215843
0.8315	Intermediate Similarity	NPC471722
0.8315	Intermediate Similarity	NPC328539
0.8315	Intermediate Similarity	NPC474677
0.8315	Intermediate Similarity	NPC193360
0.8315	Intermediate Similarity	NPC470417
0.8315	Intermediate Similarity	NPC471724
0.8295	Intermediate Similarity	NPC473168
0.8295	Intermediate Similarity	NPC475022
0.8295	Intermediate Similarity	NPC327115
0.8295	Intermediate Similarity	NPC89077
0.8295	Intermediate Similarity	NPC222613
0.8295	Intermediate Similarity	NPC118648
0.828	Intermediate Similarity	NPC49371
0.8276	Intermediate Similarity	NPC473246
0.8276	Intermediate Similarity	NPC472265
0.8261	Intermediate Similarity	NPC292793
0.8261	Intermediate Similarity	NPC111015
0.8256	Intermediate Similarity	NPC110780
0.8256	Intermediate Similarity	NPC46881
0.8242	Intermediate Similarity	NPC475806
0.8235	Intermediate Similarity	NPC2482
0.8222	Intermediate Similarity	NPC474570
0.8222	Intermediate Similarity	NPC309603
0.8222	Intermediate Similarity	NPC473999
0.8222	Intermediate Similarity	NPC54689
0.8214	Intermediate Similarity	NPC477522
0.8214	Intermediate Similarity	NPC82635
0.8211	Intermediate Similarity	NPC83709
0.8211	Intermediate Similarity	NPC154072
0.8202	Intermediate Similarity	NPC474684
0.8202	Intermediate Similarity	NPC142361
0.8202	Intermediate Similarity	NPC165895
0.8202	Intermediate Similarity	NPC136548
0.8202	Intermediate Similarity	NPC93778
0.8193	Intermediate Similarity	NPC96319
0.8191	Intermediate Similarity	NPC107243
0.8191	Intermediate Similarity	NPC18509
0.8191	Intermediate Similarity	NPC190554
0.8191	Intermediate Similarity	NPC57416
0.8182	Intermediate Similarity	NPC470574
0.8182	Intermediate Similarity	NPC202868
0.8182	Intermediate Similarity	NPC474083
0.8182	Intermediate Similarity	NPC102292
0.8172	Intermediate Similarity	NPC271195
0.8172	Intermediate Similarity	NPC472824
0.8161	Intermediate Similarity	NPC477373
0.8161	Intermediate Similarity	NPC474748
0.8152	Intermediate Similarity	NPC66429
0.8152	Intermediate Similarity	NPC250575
0.8152	Intermediate Similarity	NPC243866
0.8152	Intermediate Similarity	NPC152897
0.8152	Intermediate Similarity	NPC472942
0.8144	Intermediate Similarity	NPC191892
0.8144	Intermediate Similarity	NPC117185
0.814	Intermediate Similarity	NPC150506
0.814	Intermediate Similarity	NPC147066
0.814	Intermediate Similarity	NPC121984
0.8118	Intermediate Similarity	NPC472490
0.8111	Intermediate Similarity	NPC44181
0.8095	Intermediate Similarity	NPC198968
0.8095	Intermediate Similarity	NPC318495
0.8095	Intermediate Similarity	NPC155986
0.809	Intermediate Similarity	NPC94666
0.809	Intermediate Similarity	NPC94755
0.809	Intermediate Similarity	NPC470955
0.809	Intermediate Similarity	NPC72133
0.8085	Intermediate Similarity	NPC477853
0.8085	Intermediate Similarity	NPC155676
0.8068	Intermediate Similarity	NPC180834
0.8068	Intermediate Similarity	NPC25833
0.8068	Intermediate Similarity	NPC33913
0.8065	Intermediate Similarity	NPC196485
0.8065	Intermediate Similarity	NPC8993
0.8065	Intermediate Similarity	NPC245972
0.8061	Intermediate Similarity	NPC137657
0.8046	Intermediate Similarity	NPC328351
0.8046	Intermediate Similarity	NPC310989
0.8046	Intermediate Similarity	NPC260956
0.8046	Intermediate Similarity	NPC212083
0.8043	Intermediate Similarity	NPC23434
0.8043	Intermediate Similarity	NPC212301
0.8043	Intermediate Similarity	NPC185936
0.8043	Intermediate Similarity	NPC262870
0.8043	Intermediate Similarity	NPC131872
0.8043	Intermediate Similarity	NPC272746
0.8043	Intermediate Similarity	NPC86266
0.8043	Intermediate Similarity	NPC168027
0.8043	Intermediate Similarity	NPC110657
0.8043	Intermediate Similarity	NPC473998
0.8041	Intermediate Similarity	NPC87351
0.8041	Intermediate Similarity	NPC477915
0.8041	Intermediate Similarity	NPC185530
0.8023	Intermediate Similarity	NPC26117
0.8022	Intermediate Similarity	NPC275740
0.8022	Intermediate Similarity	NPC86319
0.8022	Intermediate Similarity	NPC474704
0.8022	Intermediate Similarity	NPC475921
0.8021	Intermediate Similarity	NPC15390
0.8021	Intermediate Similarity	NPC144956
0.8	Intermediate Similarity	NPC73064
0.8	Intermediate Similarity	NPC291634
0.8	Intermediate Similarity	NPC475894
0.8	Intermediate Similarity	NPC298904
0.8	Intermediate Similarity	NPC187376
0.8	Intermediate Similarity	NPC159046
0.8	Intermediate Similarity	NPC312215
0.8	Intermediate Similarity	NPC233836
0.8	Intermediate Similarity	NPC126815
0.8	Intermediate Similarity	NPC138756
0.798	Intermediate Similarity	NPC149047
0.798	Intermediate Similarity	NPC257353
0.798	Intermediate Similarity	NPC166607
0.7979	Intermediate Similarity	NPC127063
0.7979	Intermediate Similarity	NPC162001
0.7979	Intermediate Similarity	NPC472932
0.7979	Intermediate Similarity	NPC222845

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 NPC472484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1619
0.2-0.3	4264
0.3-0.4	2151
0.4-0.5	505
0.5-0.6	153
0.6-0.7	130
0.7-0.8	142
0.8-0.85	25
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD4786	Approved
0.8916	High Similarity	NPD3667	Approved
0.8706	High Similarity	NPD3666	Approved
0.8706	High Similarity	NPD3133	Approved
0.8706	High Similarity	NPD3665	Phase 1
0.869	High Similarity	NPD4223	Phase 3
0.869	High Similarity	NPD4221	Approved
0.8636	High Similarity	NPD4753	Phase 2
0.8556	High Similarity	NPD4202	Approved
0.8506	High Similarity	NPD3574	Clinical (unspecified phase)
0.8506	High Similarity	NPD3618	Phase 1
0.8488	Intermediate Similarity	NPD4197	Approved
0.8391	Intermediate Similarity	NPD5329	Approved
0.837	Intermediate Similarity	NPD4629	Approved
0.837	Intermediate Similarity	NPD5210	Approved
0.8295	Intermediate Similarity	NPD5205	Approved
0.8295	Intermediate Similarity	NPD4689	Approved
0.8295	Intermediate Similarity	NPD4690	Approved
0.8295	Intermediate Similarity	NPD4693	Phase 3
0.8295	Intermediate Similarity	NPD4138	Approved
0.8295	Intermediate Similarity	NPD4688	Approved
0.8222	Intermediate Similarity	NPD5328	Approved
0.8193	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD4755	Approved
0.8161	Intermediate Similarity	NPD4788	Approved
0.8152	Intermediate Similarity	NPD6399	Phase 3
0.814	Intermediate Similarity	NPD4692	Approved
0.814	Intermediate Similarity	NPD4139	Approved
0.809	Intermediate Similarity	NPD5280	Approved
0.809	Intermediate Similarity	NPD5690	Phase 2
0.809	Intermediate Similarity	NPD4694	Approved
0.8068	Intermediate Similarity	NPD3668	Phase 3
0.8043	Intermediate Similarity	NPD6079	Approved
0.8021	Intermediate Similarity	NPD4700	Approved
0.8021	Intermediate Similarity	NPD4696	Approved
0.8021	Intermediate Similarity	NPD5285	Approved
0.8021	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.7938	Intermediate Similarity	NPD5223	Approved
0.7917	Intermediate Similarity	NPD5696	Approved
0.7907	Intermediate Similarity	NPD4195	Approved
0.7895	Intermediate Similarity	NPD4697	Phase 3
0.7889	Intermediate Similarity	NPD5279	Phase 3
0.7857	Intermediate Similarity	NPD5224	Approved
0.7857	Intermediate Similarity	NPD5226	Approved
0.7857	Intermediate Similarity	NPD5225	Approved
0.7857	Intermediate Similarity	NPD4633	Approved
0.7857	Intermediate Similarity	NPD5211	Phase 2
0.7857	Intermediate Similarity	NPD6942	Approved
0.7857	Intermediate Similarity	NPD7339	Approved
0.7849	Intermediate Similarity	NPD5281	Approved
0.7849	Intermediate Similarity	NPD5284	Approved
0.7791	Intermediate Similarity	NPD3617	Approved
0.7789	Intermediate Similarity	NPD5695	Phase 3
0.7778	Intermediate Similarity	NPD4754	Approved
0.7778	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD5175	Approved
0.7738	Intermediate Similarity	NPD4785	Approved
0.7738	Intermediate Similarity	NPD4784	Approved
0.7711	Intermediate Similarity	NPD4243	Approved
0.7708	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5221	Approved
0.7708	Intermediate Similarity	NPD5222	Approved
0.77	Intermediate Similarity	NPD5141	Approved
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD6098	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7334	Approved
0.767	Intermediate Similarity	NPD4634	Approved
0.7629	Intermediate Similarity	NPD5173	Approved
0.7624	Intermediate Similarity	NPD6675	Approved
0.7624	Intermediate Similarity	NPD5739	Approved
0.7624	Intermediate Similarity	NPD7128	Approved
0.7624	Intermediate Similarity	NPD4767	Approved
0.7624	Intermediate Similarity	NPD4768	Approved
0.7624	Intermediate Similarity	NPD6402	Approved
0.7614	Intermediate Similarity	NPD4748	Discontinued
0.7609	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5133	Approved
0.7573	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD6372	Approved
0.7553	Intermediate Similarity	NPD4096	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7549	Intermediate Similarity	NPD5697	Approved
0.7527	Intermediate Similarity	NPD6903	Approved
0.7527	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4518	Approved
0.7527	Intermediate Similarity	NPD5208	Approved
0.7476	Intermediate Similarity	NPD6011	Approved
0.7476	Intermediate Similarity	NPD6881	Approved
0.7476	Intermediate Similarity	NPD6899	Approved
0.7476	Intermediate Similarity	NPD4729	Approved
0.7476	Intermediate Similarity	NPD5128	Approved
0.7476	Intermediate Similarity	NPD7320	Approved
0.7476	Intermediate Similarity	NPD4730	Approved
0.747	Intermediate Similarity	NPD3698	Phase 2
0.7447	Intermediate Similarity	NPD6673	Approved
0.7447	Intermediate Similarity	NPD6080	Approved
0.7447	Intermediate Similarity	NPD6904	Approved
0.7442	Intermediate Similarity	NPD5275	Approved
0.7442	Intermediate Similarity	NPD4190	Phase 3
0.7429	Intermediate Similarity	NPD6650	Approved
0.7429	Intermediate Similarity	NPD6649	Approved
0.7423	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7525	Registered
0.7416	Intermediate Similarity	NPD4695	Discontinued
0.7407	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD6013	Approved
0.7404	Intermediate Similarity	NPD6014	Approved
0.7391	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4244	Approved
0.7381	Intermediate Similarity	NPD4245	Approved
0.7381	Intermediate Similarity	NPD4747	Approved
0.7368	Intermediate Similarity	NPD5207	Approved
0.734	Intermediate Similarity	NPD6672	Approved
0.734	Intermediate Similarity	NPD5737	Approved
0.7333	Intermediate Similarity	NPD5135	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5249	Phase 3
0.7333	Intermediate Similarity	NPD5250	Approved
0.7333	Intermediate Similarity	NPD5169	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD5247	Approved
0.7333	Intermediate Similarity	NPD5251	Approved
0.7333	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD5248	Approved
0.7327	Intermediate Similarity	NPD5091	Approved
0.7326	Intermediate Similarity	NPD6924	Approved
0.7326	Intermediate Similarity	NPD6926	Approved
0.732	Intermediate Similarity	NPD6001	Approved
0.7312	Intermediate Similarity	NPD4623	Approved
0.7312	Intermediate Similarity	NPD4519	Discontinued
0.7294	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5693	Phase 1
0.7292	Intermediate Similarity	NPD7515	Phase 2
0.7282	Intermediate Similarity	NPD6008	Approved
0.7264	Intermediate Similarity	NPD5215	Approved
0.7264	Intermediate Similarity	NPD5127	Approved
0.7264	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5217	Approved
0.7264	Intermediate Similarity	NPD6869	Approved
0.7264	Intermediate Similarity	NPD5216	Approved
0.7264	Intermediate Similarity	NPD6847	Approved
0.7264	Intermediate Similarity	NPD8130	Phase 1
0.7264	Intermediate Similarity	NPD6617	Approved
0.7262	Intermediate Similarity	NPD4137	Phase 3
0.7262	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7196	Intermediate Similarity	NPD8297	Approved
0.7196	Intermediate Similarity	NPD6882	Approved
0.7188	Intermediate Similarity	NPD5692	Phase 3
0.7176	Intermediate Similarity	NPD4691	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.7159	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD5360	Phase 3
0.7143	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4632	Approved
0.7113	Intermediate Similarity	NPD6050	Approved
0.7113	Intermediate Similarity	NPD5694	Approved
0.7065	Intermediate Similarity	NPD4270	Approved
0.7065	Intermediate Similarity	NPD4269	Approved
0.7064	Intermediate Similarity	NPD5167	Approved
0.7054	Intermediate Similarity	NPD6059	Approved
0.7054	Intermediate Similarity	NPD6319	Approved
0.7054	Intermediate Similarity	NPD6054	Approved
0.7048	Intermediate Similarity	NPD6412	Phase 2
0.7045	Intermediate Similarity	NPD3702	Approved
0.7	Intermediate Similarity	NPD6274	Approved
0.6991	Remote Similarity	NPD6016	Approved
0.6991	Remote Similarity	NPD6015	Approved
0.6981	Remote Similarity	NPD5168	Approved
0.697	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD4522	Approved
0.6939	Remote Similarity	NPD8035	Phase 2
0.6939	Remote Similarity	NPD8034	Phase 2
0.6937	Remote Similarity	NPD6009	Approved
0.6937	Remote Similarity	NPD6317	Approved
0.6932	Remote Similarity	NPD5733	Approved
0.6932	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4058	Approved
0.6932	Remote Similarity	NPD4687	Approved
0.6931	Remote Similarity	NPD7902	Approved
0.693	Remote Similarity	NPD6370	Approved
0.693	Remote Similarity	NPD5988	Approved
0.6907	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5654	Approved
0.6897	Remote Similarity	NPD7151	Approved
0.6897	Remote Similarity	NPD7152	Approved
0.6897	Remote Similarity	NPD7150	Approved
0.6897	Remote Similarity	NPD5276	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