NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	526.382
LogP:	5.017
LogD:	4.25
LogS:	-4.793
# Rotatable Bonds:	9
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	4.862
Fsp3:	0.8
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:	-5.07
MDCK Permeability:	1.3277694961288944e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	90.69756317138672%
Volume Distribution (VD):	0.485
Pgp-substrate:	5.280248641967773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.501
CYP3A4-inhibitor:	0.23
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	5.567
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.467
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.182
Skin Sensitization:	0.059
Carcinogencity:	0.09
Eye Corrosion:	0.034
Eye Irritation:	0.044
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC477373

Natural Product ID:	NPC477373
*Common Name:**	3-[(3R,3aR,5aR,6S,7S,9bR)-3-[(2R)-6-hydroxy-6-methyl-4-oxoheptan-2-yl]-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
IUPAC Name:	3-[(3R,3aR,5aR,6S,7S,9bR)-3-[(2R)-6-hydroxy-6-methyl-4-oxoheptan-2-yl]-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
Synonyms:	Seco-coccinic acid C
Standard InCHIKey:	RUOXENRTLGLVCZ-HGFRCQJKSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-19(2)22-9-10-25-24(28(22,6)14-13-26(32)33)12-16-29(7)23(11-15-30(25,29)8)20(3)17-21(31)18-27(4,5)34/h10,20,22-24,34H,1,9,11-18H2,2-8H3,(H,32,33)/t20-,22+,23-,24+,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC(=O)CC(C)(C)O)[C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC[C@H]([C@]3(C)CCC(=O)O)C(=C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44585545
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	12100	nM	PMID[18491866]

☑ 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 NPC477373 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	1099
0.2-0.3	6098
0.3-0.4	14851
0.4-0.5	7505
0.5-0.6	6637
0.6-0.7	4720
0.7-0.8	1477
0.8-0.85	130
0.85-0.9	23
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC477371
0.9367	High Similarity	NPC133391
0.9268	High Similarity	NPC96496
0.9241	High Similarity	NPC38350
0.9241	High Similarity	NPC147066
0.9241	High Similarity	NPC201912
0.9241	High Similarity	NPC477372
0.9125	High Similarity	NPC260956
0.9048	High Similarity	NPC474570
0.9036	High Similarity	NPC136948
0.9012	High Similarity	NPC69279
0.9012	High Similarity	NPC83569
0.8889	High Similarity	NPC320514
0.8861	High Similarity	NPC321514
0.8824	High Similarity	NPC262043
0.8795	High Similarity	NPC29447
0.8795	High Similarity	NPC269638
0.878	High Similarity	NPC168188
0.878	High Similarity	NPC470015
0.878	High Similarity	NPC310470
0.875	High Similarity	NPC158846
0.875	High Similarity	NPC196827
0.875	High Similarity	NPC274996
0.875	High Similarity	NPC215843
0.8675	High Similarity	NPC165064
0.8675	High Similarity	NPC164577
0.8659	High Similarity	NPC240302
0.8642	High Similarity	NPC37038
0.8625	High Similarity	NPC179028
0.8621	High Similarity	NPC204341
0.8608	High Similarity	NPC180886
0.8588	High Similarity	NPC167877
0.8588	High Similarity	NPC128644
0.8571	High Similarity	NPC94531
0.8571	High Similarity	NPC123319
0.8571	High Similarity	NPC311702
0.8571	High Similarity	NPC160817
0.8554	High Similarity	NPC477852
0.8554	High Similarity	NPC167103
0.8554	High Similarity	NPC97913
0.8539	High Similarity	NPC263347
0.8537	High Similarity	NPC278459
0.8537	High Similarity	NPC327002
0.8519	High Similarity	NPC231431
0.85	High Similarity	NPC66105
0.8488	Intermediate Similarity	NPC117122
0.8471	Intermediate Similarity	NPC155011
0.8471	Intermediate Similarity	NPC472869
0.8471	Intermediate Similarity	NPC262085
0.8452	Intermediate Similarity	NPC472865
0.8452	Intermediate Similarity	NPC472480
0.8434	Intermediate Similarity	NPC296367
0.8434	Intermediate Similarity	NPC193347
0.8427	Intermediate Similarity	NPC124207
0.8409	Intermediate Similarity	NPC154101
0.8395	Intermediate Similarity	NPC280654
0.8395	Intermediate Similarity	NPC321690
0.8395	Intermediate Similarity	NPC74410
0.8395	Intermediate Similarity	NPC110094
0.8395	Intermediate Similarity	NPC260385
0.8391	Intermediate Similarity	NPC475921
0.8391	Intermediate Similarity	NPC54689
0.8391	Intermediate Similarity	NPC474704
0.8391	Intermediate Similarity	NPC215029
0.8391	Intermediate Similarity	NPC476733
0.8375	Intermediate Similarity	NPC20466
0.8375	Intermediate Similarity	NPC246445
0.8372	Intermediate Similarity	NPC173089
0.8372	Intermediate Similarity	NPC142361
0.8372	Intermediate Similarity	NPC159046
0.8372	Intermediate Similarity	NPC233836
0.8372	Intermediate Similarity	NPC158141
0.8372	Intermediate Similarity	NPC171722
0.8372	Intermediate Similarity	NPC90652
0.8372	Intermediate Similarity	NPC474684
0.8372	Intermediate Similarity	NPC187376
0.8372	Intermediate Similarity	NPC312215
0.8353	Intermediate Similarity	NPC11711
0.8353	Intermediate Similarity	NPC473038
0.8353	Intermediate Similarity	NPC142649
0.8353	Intermediate Similarity	NPC201655
0.8333	Intermediate Similarity	NPC171395
0.8315	Intermediate Similarity	NPC243866
0.8315	Intermediate Similarity	NPC66429
0.8315	Intermediate Similarity	NPC474807
0.8315	Intermediate Similarity	NPC152897
0.8313	Intermediate Similarity	NPC274050
0.8313	Intermediate Similarity	NPC162632
0.8313	Intermediate Similarity	NPC44963
0.8313	Intermediate Similarity	NPC267691
0.8313	Intermediate Similarity	NPC232625
0.8313	Intermediate Similarity	NPC472684
0.8313	Intermediate Similarity	NPC263272
0.8313	Intermediate Similarity	NPC471898
0.8313	Intermediate Similarity	NPC142244
0.8295	Intermediate Similarity	NPC471896
0.8295	Intermediate Similarity	NPC111585
0.8295	Intermediate Similarity	NPC175628
0.8295	Intermediate Similarity	NPC469400
0.8295	Intermediate Similarity	NPC148414
0.8293	Intermediate Similarity	NPC192744
0.8293	Intermediate Similarity	NPC327674
0.8293	Intermediate Similarity	NPC199595
0.8276	Intermediate Similarity	NPC72397
0.8276	Intermediate Similarity	NPC472870
0.8276	Intermediate Similarity	NPC294480
0.8276	Intermediate Similarity	NPC1753
0.8276	Intermediate Similarity	NPC242864
0.8276	Intermediate Similarity	NPC474511
0.8276	Intermediate Similarity	NPC328313
0.8276	Intermediate Similarity	NPC470417
0.8272	Intermediate Similarity	NPC471899
0.8272	Intermediate Similarity	NPC107039
0.8272	Intermediate Similarity	NPC165711
0.8272	Intermediate Similarity	NPC471897
0.8256	Intermediate Similarity	NPC186975
0.8256	Intermediate Similarity	NPC212843
0.8256	Intermediate Similarity	NPC28252
0.8256	Intermediate Similarity	NPC55309
0.825	Intermediate Similarity	NPC192540
0.825	Intermediate Similarity	NPC279666
0.8242	Intermediate Similarity	NPC155676
0.8242	Intermediate Similarity	NPC29152
0.8235	Intermediate Similarity	NPC59453
0.8235	Intermediate Similarity	NPC473246
0.8235	Intermediate Similarity	NPC100391
0.8235	Intermediate Similarity	NPC19849
0.8235	Intermediate Similarity	NPC209882
0.8235	Intermediate Similarity	NPC476038
0.8235	Intermediate Similarity	NPC214043
0.8235	Intermediate Similarity	NPC194937
0.8235	Intermediate Similarity	NPC472864
0.8235	Intermediate Similarity	NPC221758
0.8235	Intermediate Similarity	NPC85774
0.8235	Intermediate Similarity	NPC82902
0.8235	Intermediate Similarity	NPC96095
0.8235	Intermediate Similarity	NPC144258
0.8235	Intermediate Similarity	NPC156981
0.8214	Intermediate Similarity	NPC321289
0.8214	Intermediate Similarity	NPC69101
0.8214	Intermediate Similarity	NPC251779
0.8214	Intermediate Similarity	NPC327969
0.8202	Intermediate Similarity	NPC86266
0.8202	Intermediate Similarity	NPC110657
0.8202	Intermediate Similarity	NPC26888
0.8202	Intermediate Similarity	NPC189520
0.8202	Intermediate Similarity	NPC212301
0.8202	Intermediate Similarity	NPC297265
0.8193	Intermediate Similarity	NPC104545
0.8182	Intermediate Similarity	NPC474889
0.8182	Intermediate Similarity	NPC474700
0.8182	Intermediate Similarity	NPC84271
0.8182	Intermediate Similarity	NPC102414
0.8182	Intermediate Similarity	NPC214387
0.8182	Intermediate Similarity	NPC77168
0.8182	Intermediate Similarity	NPC155479
0.8182	Intermediate Similarity	NPC474245
0.8182	Intermediate Similarity	NPC32830
0.8182	Intermediate Similarity	NPC305039
0.8171	Intermediate Similarity	NPC471409
0.8171	Intermediate Similarity	NPC275494
0.8161	Intermediate Similarity	NPC236618
0.8161	Intermediate Similarity	NPC317590
0.8161	Intermediate Similarity	NPC472481
0.8161	Intermediate Similarity	NPC472482
0.8161	Intermediate Similarity	NPC472484
0.8152	Intermediate Similarity	NPC156546
0.8152	Intermediate Similarity	NPC57416
0.8152	Intermediate Similarity	NPC107243
0.8148	Intermediate Similarity	NPC89294
0.8148	Intermediate Similarity	NPC309399
0.8148	Intermediate Similarity	NPC69143
0.814	Intermediate Similarity	NPC470223
0.814	Intermediate Similarity	NPC471224
0.814	Intermediate Similarity	NPC283733
0.814	Intermediate Similarity	NPC474218
0.814	Intermediate Similarity	NPC469948
0.814	Intermediate Similarity	NPC474083
0.8132	Intermediate Similarity	NPC88310
0.8132	Intermediate Similarity	NPC469599
0.8125	Intermediate Similarity	NPC241854
0.8125	Intermediate Similarity	NPC301065
0.8125	Intermediate Similarity	NPC476046
0.8125	Intermediate Similarity	NPC161923
0.8125	Intermediate Similarity	NPC183503
0.8125	Intermediate Similarity	NPC251970
0.8125	Intermediate Similarity	NPC103958
0.8125	Intermediate Similarity	NPC283908
0.8118	Intermediate Similarity	NPC476100
0.8118	Intermediate Similarity	NPC476082
0.8118	Intermediate Similarity	NPC278648
0.8118	Intermediate Similarity	NPC70834
0.8118	Intermediate Similarity	NPC472492
0.8111	Intermediate Similarity	NPC470376
0.8111	Intermediate Similarity	NPC170220
0.8111	Intermediate Similarity	NPC470375
0.8111	Intermediate Similarity	NPC107674
0.8111	Intermediate Similarity	NPC141497
0.8111	Intermediate Similarity	NPC206810
0.8105	Intermediate Similarity	NPC474330

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 NPC477373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1533
0.2-0.3	4172
0.3-0.4	2187
0.4-0.5	612
0.5-0.6	212
0.6-0.7	162
0.7-0.8	116
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD4221	Approved
0.8434	Intermediate Similarity	NPD4223	Phase 3
0.8409	Intermediate Similarity	NPD5284	Approved
0.8409	Intermediate Similarity	NPD5281	Approved
0.8353	Intermediate Similarity	NPD5329	Approved
0.8315	Intermediate Similarity	NPD6399	Phase 3
0.8256	Intermediate Similarity	NPD6098	Approved
0.8256	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4786	Approved
0.8235	Intermediate Similarity	NPD4197	Approved
0.8182	Intermediate Similarity	NPD6904	Approved
0.8182	Intermediate Similarity	NPD6080	Approved
0.8182	Intermediate Similarity	NPD6673	Approved
0.8152	Intermediate Similarity	NPD6084	Phase 2
0.8152	Intermediate Similarity	NPD6083	Phase 2
0.8132	Intermediate Similarity	NPD5695	Phase 3
0.8068	Intermediate Similarity	NPD6672	Approved
0.8068	Intermediate Similarity	NPD5737	Approved
0.8046	Intermediate Similarity	NPD4689	Approved
0.8046	Intermediate Similarity	NPD5690	Phase 2
0.8046	Intermediate Similarity	NPD4694	Approved
0.8046	Intermediate Similarity	NPD4138	Approved
0.8046	Intermediate Similarity	NPD4688	Approved
0.8046	Intermediate Similarity	NPD4693	Phase 3
0.8046	Intermediate Similarity	NPD5280	Approved
0.8046	Intermediate Similarity	NPD4690	Approved
0.8046	Intermediate Similarity	NPD5205	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD6050	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7889	Intermediate Similarity	NPD5692	Phase 3
0.7882	Intermediate Similarity	NPD4692	Approved
0.7882	Intermediate Similarity	NPD4139	Approved
0.7872	Intermediate Similarity	NPD5696	Approved
0.7865	Intermediate Similarity	NPD5208	Approved
0.7841	Intermediate Similarity	NPD6684	Approved
0.7841	Intermediate Similarity	NPD7146	Approved
0.7841	Intermediate Similarity	NPD7521	Approved
0.7841	Intermediate Similarity	NPD7334	Approved
0.7841	Intermediate Similarity	NPD6409	Approved
0.7841	Intermediate Similarity	NPD5330	Approved
0.7816	Intermediate Similarity	NPD3665	Phase 1
0.7816	Intermediate Similarity	NPD3666	Approved
0.7816	Intermediate Similarity	NPD3133	Approved
0.7802	Intermediate Similarity	NPD5693	Phase 1
0.7802	Intermediate Similarity	NPD5694	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7742	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3617	Approved
0.7692	Intermediate Similarity	NPD5207	Approved
0.7667	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6903	Approved
0.7654	Intermediate Similarity	NPD4243	Approved
0.7647	Intermediate Similarity	NPD4195	Approved
0.764	Intermediate Similarity	NPD3618	Phase 1
0.764	Intermediate Similarity	NPD5279	Phase 3
0.7614	Intermediate Similarity	NPD3668	Phase 3
0.7609	Intermediate Similarity	NPD6079	Approved
0.7609	Intermediate Similarity	NPD7515	Phase 2
0.7582	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7128	Approved
0.7576	Intermediate Similarity	NPD5739	Approved
0.7576	Intermediate Similarity	NPD6675	Approved
0.7576	Intermediate Similarity	NPD6402	Approved
0.7558	Intermediate Similarity	NPD4695	Discontinued
0.7553	Intermediate Similarity	NPD4629	Approved
0.7553	Intermediate Similarity	NPD5210	Approved
0.7531	Intermediate Similarity	NPD4747	Approved
0.7529	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD4096	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7471	Intermediate Similarity	NPD5369	Approved
0.747	Intermediate Similarity	NPD5733	Approved
0.747	Intermediate Similarity	NPD4784	Approved
0.747	Intermediate Similarity	NPD4785	Approved
0.7447	Intermediate Similarity	NPD7748	Approved
0.7447	Intermediate Similarity	NPD6001	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7444	Intermediate Similarity	NPD4623	Approved
0.7439	Intermediate Similarity	NPD6081	Approved
0.7426	Intermediate Similarity	NPD6899	Approved
0.7426	Intermediate Similarity	NPD7320	Approved
0.7426	Intermediate Similarity	NPD6881	Approved
0.7407	Intermediate Similarity	NPD4137	Phase 3
0.7396	Intermediate Similarity	NPD4755	Approved
0.7368	Intermediate Similarity	NPD5654	Approved
0.7353	Intermediate Similarity	NPD6373	Approved
0.7353	Intermediate Similarity	NPD6372	Approved
0.734	Intermediate Similarity	NPD5133	Approved
0.7327	Intermediate Similarity	NPD5701	Approved
0.7327	Intermediate Similarity	NPD5697	Approved
0.7317	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7284	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4518	Approved
0.7282	Intermediate Similarity	NPD7102	Approved
0.7282	Intermediate Similarity	NPD6883	Approved
0.7282	Intermediate Similarity	NPD7290	Approved
0.7262	Intermediate Similarity	NPD4687	Approved
0.7255	Intermediate Similarity	NPD6011	Approved
0.725	Intermediate Similarity	NPD4224	Phase 2
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7245	Intermediate Similarity	NPD6404	Discontinued
0.7245	Intermediate Similarity	NPD4696	Approved
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD6411	Approved
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7229	Intermediate Similarity	NPD5276	Approved
0.7216	Intermediate Similarity	NPD5959	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7216	Intermediate Similarity	NPD7902	Approved
0.7212	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6617	Approved
0.7212	Intermediate Similarity	NPD6869	Approved
0.7212	Intermediate Similarity	NPD8130	Phase 1
0.7212	Intermediate Similarity	NPD6650	Approved
0.7212	Intermediate Similarity	NPD6847	Approved
0.7212	Intermediate Similarity	NPD6649	Approved
0.72	Intermediate Similarity	NPD6052	Approved
0.7196	Intermediate Similarity	NPD7115	Discovery
0.7191	Intermediate Similarity	NPD4270	Approved
0.7191	Intermediate Similarity	NPD4269	Approved
0.7184	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD6012	Approved
0.7184	Intermediate Similarity	NPD6014	Approved
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD4190	Phase 3
0.7176	Intermediate Similarity	NPD5275	Approved
0.7176	Intermediate Similarity	NPD7339	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7159	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7113	Intermediate Similarity	NPD7614	Phase 1
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD5091	Approved
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.7073	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5360	Phase 3
0.7059	Intermediate Similarity	NPD4058	Approved
0.7059	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6926	Approved
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7037	Intermediate Similarity	NPD7331	Phase 2
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD4754	Approved
0.7021	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6101	Approved
0.7021	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6614	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD5368	Approved
0.6966	Remote Similarity	NPD4252	Approved
0.6961	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6952	Remote Similarity	NPD4634	Approved
0.6947	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD5362	Discontinued
0.6916	Remote Similarity	NPD4632	Approved
0.6914	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7341	Phase 2
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7900	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6897	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6117	Approved
0.6897	Remote Similarity	NPD6933	Approved
0.6893	Remote Similarity	NPD6008	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6893	Remote Similarity	NPD4768	Approved
0.6882	Remote Similarity	NPD5786	Approved
0.686	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6319	Approved
0.6827	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD6335	Approved
0.6818	Remote Similarity	NPD6116	Phase 1
0.6813	Remote Similarity	NPD6435	Approved
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.6789	Remote Similarity	NPD6274	Approved
0.6789	Remote Similarity	NPD6868	Approved
0.6782	Remote Similarity	NPD3702	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6757	Remote Similarity	NPD7100	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