NPASS Compound

Structure

NPC185617 OpenBabel07101718222D 35 39 0 0 1 0 0 0 0 0999 V2000 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -6.0622 -1.5000 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 -1.7321 1.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 28 1 0 0 0 0 6 35 1 0 0 0 0 7 9 1 0 0 0 0 7 26 1 0 0 0 0 8 10 1 0 0 0 0 8 27 1 0 0 0 0 9 29 1 0 0 0 0 10 28 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 1 1 1 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 16 27 1 0 0 0 0 17 22 1 0 0 0 0 17 30 2 0 0 0 0 18 24 2 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 20 26 1 6 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 29 1 0 0 0 0 22 23 2 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 35 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 2 1 1 0 0 0 27 3 1 1 0 0 0 28 29 1 6 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.25
Volume:	501.644
LogP:	3.773
LogD:	2.258
LogS:	-4.212
# Rotatable Bonds:	2
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	4.795
Fsp3:	0.621
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.518
MDCK Permeability:	1.4635535080742557e-05
Pgp-inhibitor:	0.381
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.64

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	96.07756805419922%
Volume Distribution (VD):	0.358
Pgp-substrate:	6.974074363708496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.714

ADMET: Excretion

Clearance (CL):	4.995
Half-life (T1/2):	0.58

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.57
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.573
Skin Sensitization:	0.038
Carcinogencity:	0.837
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC185617

Natural Product ID:	NPC185617
*Common Name:**	3-Methoxy-6-Oxotingenol-23-Oic Acid
IUPAC Name:	(6aS,6bS,8aS,11R,12aR,14aR)-2-hydroxy-3-methoxy-6a,6b,8a,11,14a-pentamethyl-5,10-dioxo-7,8,9,11,12,12a,13,14-octahydropicene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	YFACGTSGIRUGSE-HVTWXBLKSA-N
Standard InCHI:	InChI=1S/C29H36O6/c1-15-11-20-26(2,14-19(15)32)7-9-29(5)21-13-17(30)22-16(27(21,3)8-10-28(20,29)4)12-18(31)24(35-6)23(22)25(33)34/h12-13,15,20,31H,7-11,14H2,1-6H3,(H,33,34)/t15-,20-,26+,27+,28+,29-/m1/s1
SMILES:	COc1c(O)cc2c(c1C(=O)O)C(=O)C=C1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2C[C@@H](C)C(=O)C1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651339
PubChem CID:	50907763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO25224	Maytenus retusa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090801]
NPO25224	Maytenus retusa	Species	Celastraceae	Eukaryota	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	11.0	%	PMID[468497]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	17.0	%	PMID[468497]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	15.0	%	PMID[468497]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	59.0	%	PMID[468497]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	57.0	%	PMID[468497]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	78.0	%	PMID[468497]

☑ 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 NPC185617 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	393
0.1-0.2	1671
0.2-0.3	3454
0.3-0.4	7616
0.4-0.5	9757
0.5-0.6	5917
0.6-0.7	7009
0.7-0.8	6622
0.8-0.85	241
0.85-0.9	12
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9272	High Similarity	NPC10842
0.894	High Similarity	NPC184935
0.891	High Similarity	NPC124842
0.8889	High Similarity	NPC470038
0.8854	High Similarity	NPC164912
0.8846	High Similarity	NPC470037
0.8805	High Similarity	NPC279605
0.8797	High Similarity	NPC62051
0.879	High Similarity	NPC118427
0.879	High Similarity	NPC144283
0.8701	High Similarity	NPC309169
0.8701	High Similarity	NPC196941
0.8693	High Similarity	NPC11314
0.8659	High Similarity	NPC26386
0.8654	High Similarity	NPC52692
0.8654	High Similarity	NPC470757
0.8645	High Similarity	NPC73416
0.8645	High Similarity	NPC160777
0.8634	High Similarity	NPC199463
0.8634	High Similarity	NPC37543
0.8616	High Similarity	NPC161778
0.8609	High Similarity	NPC277559
0.8596	High Similarity	NPC182693
0.859	High Similarity	NPC58752
0.8571	High Similarity	NPC5379
0.8571	High Similarity	NPC14561
0.8571	High Similarity	NPC77807
0.8563	High Similarity	NPC472803
0.8562	High Similarity	NPC273248
0.8562	High Similarity	NPC470035
0.8554	High Similarity	NPC472622
0.8553	High Similarity	NPC302783
0.8553	High Similarity	NPC473201
0.8544	High Similarity	NPC134293
0.8544	High Similarity	NPC303989
0.8544	High Similarity	NPC237441
0.8537	High Similarity	NPC144843
0.8528	High Similarity	NPC155302
0.8528	High Similarity	NPC84571
0.8528	High Similarity	NPC161947
0.8526	High Similarity	NPC258856
0.8526	High Similarity	NPC75295
0.8521	High Similarity	NPC294149
0.8519	High Similarity	NPC178976
0.8512	High Similarity	NPC472620
0.8512	High Similarity	NPC158226
0.8509	High Similarity	NPC472048
0.8506	High Similarity	NPC84273
0.8503	High Similarity	NPC163130
0.8503	High Similarity	NPC165979
0.85	High Similarity	NPC312338
0.85	High Similarity	NPC149889
0.8494	Intermediate Similarity	NPC472621
0.8491	Intermediate Similarity	NPC473680
0.8491	Intermediate Similarity	NPC473579
0.8491	Intermediate Similarity	NPC475454
0.8491	Intermediate Similarity	NPC475311
0.8487	Intermediate Similarity	NPC49911
0.8481	Intermediate Similarity	NPC55327
0.8476	Intermediate Similarity	NPC87431
0.8476	Intermediate Similarity	NPC311740
0.8466	Intermediate Similarity	NPC45846
0.8466	Intermediate Similarity	NPC470339
0.8457	Intermediate Similarity	NPC470762
0.8457	Intermediate Similarity	NPC474167
0.8452	Intermediate Similarity	NPC169214
0.8452	Intermediate Similarity	NPC229218
0.8452	Intermediate Similarity	NPC192597
0.8452	Intermediate Similarity	NPC141817
0.8452	Intermediate Similarity	NPC176030
0.8447	Intermediate Similarity	NPC127172
0.8447	Intermediate Similarity	NPC305710
0.8447	Intermediate Similarity	NPC107109
0.8438	Intermediate Similarity	NPC473773
0.8438	Intermediate Similarity	NPC75377
0.8438	Intermediate Similarity	NPC475579
0.8428	Intermediate Similarity	NPC142654
0.8424	Intermediate Similarity	NPC149389
0.8415	Intermediate Similarity	NPC472055
0.8415	Intermediate Similarity	NPC47623
0.8415	Intermediate Similarity	NPC297212
0.8408	Intermediate Similarity	NPC225351
0.8402	Intermediate Similarity	NPC4200
0.8397	Intermediate Similarity	NPC199936
0.8395	Intermediate Similarity	NPC234485
0.8393	Intermediate Similarity	NPC472619
0.8393	Intermediate Similarity	NPC99613
0.8393	Intermediate Similarity	NPC188079
0.8393	Intermediate Similarity	NPC49487
0.8385	Intermediate Similarity	NPC295646
0.8383	Intermediate Similarity	NPC200726
0.8383	Intermediate Similarity	NPC29160
0.8375	Intermediate Similarity	NPC31132
0.8375	Intermediate Similarity	NPC118033
0.8373	Intermediate Similarity	NPC220313
0.8373	Intermediate Similarity	NPC249181
0.8373	Intermediate Similarity	NPC476822
0.8373	Intermediate Similarity	NPC29055
0.8373	Intermediate Similarity	NPC12461
0.8373	Intermediate Similarity	NPC236132
0.8372	Intermediate Similarity	NPC120102
0.8372	Intermediate Similarity	NPC473785
0.8364	Intermediate Similarity	NPC40491
0.8364	Intermediate Similarity	NPC278052
0.8364	Intermediate Similarity	NPC278427
0.8364	Intermediate Similarity	NPC472906
0.8354	Intermediate Similarity	NPC46736
0.8354	Intermediate Similarity	NPC315157
0.8354	Intermediate Similarity	NPC197856
0.8354	Intermediate Similarity	NPC235448
0.8344	Intermediate Similarity	NPC476282
0.8333	Intermediate Similarity	NPC476306
0.8333	Intermediate Similarity	NPC477047
0.8333	Intermediate Similarity	NPC234331
0.8333	Intermediate Similarity	NPC177362
0.8333	Intermediate Similarity	NPC477048
0.8333	Intermediate Similarity	NPC126204
0.8323	Intermediate Similarity	NPC191930
0.8323	Intermediate Similarity	NPC472838
0.8323	Intermediate Similarity	NPC306011
0.8314	Intermediate Similarity	NPC207467
0.8313	Intermediate Similarity	NPC206605
0.8313	Intermediate Similarity	NPC215612
0.8303	Intermediate Similarity	NPC14353
0.8303	Intermediate Similarity	NPC476280
0.8303	Intermediate Similarity	NPC228785
0.8303	Intermediate Similarity	NPC141574
0.8303	Intermediate Similarity	NPC320359
0.8303	Intermediate Similarity	NPC56085
0.8302	Intermediate Similarity	NPC58373
0.8294	Intermediate Similarity	NPC473113
0.8293	Intermediate Similarity	NPC67197
0.8293	Intermediate Similarity	NPC167098
0.8293	Intermediate Similarity	NPC35598
0.8293	Intermediate Similarity	NPC180011
0.8293	Intermediate Similarity	NPC296044
0.8293	Intermediate Similarity	NPC179732
0.8293	Intermediate Similarity	NPC302258
0.8293	Intermediate Similarity	NPC143328
0.8293	Intermediate Similarity	NPC222689
0.8293	Intermediate Similarity	NPC268602
0.8293	Intermediate Similarity	NPC219867
0.8293	Intermediate Similarity	NPC283301
0.8291	Intermediate Similarity	NPC478019
0.8284	Intermediate Similarity	NPC266545
0.8284	Intermediate Similarity	NPC476637
0.8284	Intermediate Similarity	NPC475805
0.8284	Intermediate Similarity	NPC202428
0.8284	Intermediate Similarity	NPC300307
0.8282	Intermediate Similarity	NPC38898
0.8282	Intermediate Similarity	NPC16082
0.8282	Intermediate Similarity	NPC82592
0.8282	Intermediate Similarity	NPC79998
0.8274	Intermediate Similarity	NPC469394
0.8274	Intermediate Similarity	NPC20237
0.8274	Intermediate Similarity	NPC472452
0.8274	Intermediate Similarity	NPC263212
0.8274	Intermediate Similarity	NPC39091
0.8272	Intermediate Similarity	NPC268992
0.8272	Intermediate Similarity	NPC180388
0.8272	Intermediate Similarity	NPC51824
0.8272	Intermediate Similarity	NPC470337
0.8272	Intermediate Similarity	NPC113608
0.8272	Intermediate Similarity	NPC470338
0.8263	Intermediate Similarity	NPC248638
0.8263	Intermediate Similarity	NPC476295
0.8263	Intermediate Similarity	NPC7483
0.8263	Intermediate Similarity	NPC236521
0.8263	Intermediate Similarity	NPC477689
0.8263	Intermediate Similarity	NPC152659
0.8263	Intermediate Similarity	NPC474350
0.8263	Intermediate Similarity	NPC146134
0.8263	Intermediate Similarity	NPC270837
0.8261	Intermediate Similarity	NPC472279
0.8261	Intermediate Similarity	NPC295977
0.8261	Intermediate Similarity	NPC58310
0.8258	Intermediate Similarity	NPC223336
0.8256	Intermediate Similarity	NPC475054
0.8256	Intermediate Similarity	NPC478050
0.8256	Intermediate Similarity	NPC216307
0.8253	Intermediate Similarity	NPC32694
0.8253	Intermediate Similarity	NPC57715
0.8253	Intermediate Similarity	NPC61010
0.8253	Intermediate Similarity	NPC318081
0.8253	Intermediate Similarity	NPC266365
0.825	Intermediate Similarity	NPC474306
0.825	Intermediate Similarity	NPC475848
0.8242	Intermediate Similarity	NPC100123
0.8242	Intermediate Similarity	NPC326084
0.8242	Intermediate Similarity	NPC472617
0.8242	Intermediate Similarity	NPC477410
0.8239	Intermediate Similarity	NPC105591
0.8235	Intermediate Similarity	NPC124470
0.8235	Intermediate Similarity	NPC101107
0.8235	Intermediate Similarity	NPC109827
0.8232	Intermediate Similarity	NPC25850
0.8232	Intermediate Similarity	NPC150227
0.8232	Intermediate Similarity	NPC472050
0.8232	Intermediate Similarity	NPC474360
0.8232	Intermediate Similarity	NPC54928

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 NPC185617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	989
0.2-0.3	1792
0.3-0.4	2640
0.4-0.5	1966
0.5-0.6	939
0.6-0.7	374
0.7-0.8	99
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.872	High Similarity	NPD7473	Discontinued
0.8537	High Similarity	NPD6232	Discontinued
0.8229	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7458	Discontinued
0.8038	Intermediate Similarity	NPD8166	Discontinued
0.7925	Intermediate Similarity	NPD7003	Approved
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7892	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD2801	Approved
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1934	Approved
0.7824	Intermediate Similarity	NPD6959	Discontinued
0.7798	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1465	Phase 2
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD2532	Approved
0.773	Intermediate Similarity	NPD2533	Approved
0.7714	Intermediate Similarity	NPD7074	Phase 3
0.7688	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7819	Suspended
0.7657	Intermediate Similarity	NPD7054	Approved
0.7651	Intermediate Similarity	NPD3226	Approved
0.764	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD8312	Approved
0.7633	Intermediate Similarity	NPD3817	Phase 2
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7614	Intermediate Similarity	NPD7472	Approved
0.7611	Intermediate Similarity	NPD8150	Discontinued
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD7228	Approved
0.7588	Intermediate Similarity	NPD3882	Suspended
0.7571	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.7561	Intermediate Similarity	NPD1511	Approved
0.7558	Intermediate Similarity	NPD5494	Approved
0.7556	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7075	Discontinued
0.7532	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6651	Approved
0.7471	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1512	Approved
0.7453	Intermediate Similarity	NPD5408	Approved
0.7453	Intermediate Similarity	NPD5406	Approved
0.7453	Intermediate Similarity	NPD5404	Approved
0.7453	Intermediate Similarity	NPD5405	Approved
0.743	Intermediate Similarity	NPD7251	Discontinued
0.7427	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2800	Approved
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.7414	Intermediate Similarity	NPD8127	Discontinued
0.741	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD8151	Discontinued
0.7396	Intermediate Similarity	NPD6599	Discontinued
0.7389	Intermediate Similarity	NPD7808	Phase 3
0.7386	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4966	Approved
0.7384	Intermediate Similarity	NPD7768	Phase 2
0.7384	Intermediate Similarity	NPD4965	Approved
0.7384	Intermediate Similarity	NPD4967	Phase 2
0.7374	Intermediate Similarity	NPD6797	Phase 2
0.7365	Intermediate Similarity	NPD6273	Approved
0.7353	Intermediate Similarity	NPD7411	Suspended
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.731	Intermediate Similarity	NPD6801	Discontinued
0.7294	Intermediate Similarity	NPD7028	Phase 2
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3750	Approved
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD6776	Approved
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.7263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD9494	Approved
0.7253	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD943	Approved
0.725	Intermediate Similarity	NPD3620	Phase 2
0.7246	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3749	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD230	Phase 1
0.7202	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1283	Approved
0.7178	Intermediate Similarity	NPD1510	Phase 2
0.7178	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.716	Intermediate Similarity	NPD1607	Approved
0.715	Intermediate Similarity	NPD7697	Approved
0.715	Intermediate Similarity	NPD7698	Approved
0.715	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1240	Approved
0.7134	Intermediate Similarity	NPD1470	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7119	Intermediate Similarity	NPD7199	Phase 2
0.7115	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7871	Phase 2
0.7113	Intermediate Similarity	NPD7870	Phase 2
0.7113	Intermediate Similarity	NPD8320	Phase 1
0.7113	Intermediate Similarity	NPD8319	Approved
0.7111	Intermediate Similarity	NPD3751	Discontinued
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1933	Approved
0.7092	Intermediate Similarity	NPD7701	Phase 2
0.7091	Intermediate Similarity	NPD2344	Approved
0.7089	Intermediate Similarity	NPD2798	Approved
0.7083	Intermediate Similarity	NPD3300	Phase 2
0.7081	Intermediate Similarity	NPD8032	Phase 2
0.7078	Intermediate Similarity	NPD4626	Approved
0.7071	Intermediate Similarity	NPD7801	Approved
0.7066	Intermediate Similarity	NPD4110	Phase 3
0.7066	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6873	Phase 2
0.7049	Intermediate Similarity	NPD6559	Discontinued
0.7039	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5402	Approved
0.7019	Intermediate Similarity	NPD3268	Approved
0.7012	Intermediate Similarity	NPD7097	Phase 1
0.701	Intermediate Similarity	NPD6823	Phase 2
0.7006	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD6535	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1281	Approved
0.6987	Remote Similarity	NPD1201	Approved
0.6985	Remote Similarity	NPD7783	Phase 2
0.6985	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3787	Discontinued
0.6979	Remote Similarity	NPD7700	Phase 2
0.6979	Remote Similarity	NPD7699	Phase 2
0.697	Remote Similarity	NPD3748	Approved
0.6964	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7095	Approved
0.6947	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6213	Phase 3
0.6947	Remote Similarity	NPD6212	Phase 3
0.6946	Remote Similarity	NPD1549	Phase 2
0.6944	Remote Similarity	NPD3926	Phase 2
0.6943	Remote Similarity	NPD3972	Approved
0.6935	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2979	Phase 3
0.6932	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2438	Suspended
0.6923	Remote Similarity	NPD6190	Approved
0.6923	Remote Similarity	NPD2309	Approved
0.6918	Remote Similarity	NPD2797	Approved
0.6918	Remote Similarity	NPD1203	Approved
0.691	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6832	Phase 2
0.689	Remote Similarity	NPD6355	Discontinued
0.6889	Remote Similarity	NPD7229	Phase 3
0.6886	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7286	Phase 2
0.6882	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD8455	Phase 2
0.6871	Remote Similarity	NPD6663	Approved
0.6859	Remote Similarity	NPD2932	Approved
0.6859	Remote Similarity	NPD3019	Approved
0.6856	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9717	Approved
0.6835	Remote Similarity	NPD9269	Phase 2
0.6833	Remote Similarity	NPD1247	Approved
0.6832	Remote Similarity	NPD5736	Approved
0.6831	Remote Similarity	NPD7177	Discontinued
0.6826	Remote Similarity	NPD2796	Approved
0.6821	Remote Similarity	NPD920	Approved
0.6821	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD9493	Approved
0.6813	Remote Similarity	NPD1164	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