NPASS Compound

Structure

NPC163372 OpenBabel07101718272D 35 38 0 0 1 0 0 0 0 0999 V2000 -7.1527 -1.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 -4.1270 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 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 -2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7926 -3.3838 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 -1.7321 -0.0000 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 -7.7707 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0798 -4.5428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4399 -2.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 6 0 0 0 16 18 1 0 0 0 0 17 3 1 1 0 0 0 17 26 1 0 0 0 0 18 28 1 1 0 0 0 19 24 1 0 0 0 0 19 28 1 1 0 0 0 20 24 1 0 0 0 0 20 30 1 1 0 0 0 21 25 1 0 0 0 0 21 31 2 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 24 25 2 0 0 0 0 25 27 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 6 1 6 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	515.473
LogP:	3.817
LogD:	3.086
LogS:	-4.075
# Rotatable Bonds:	5
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	5.235
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.295
MDCK Permeability:	1.5861982319620438e-05
Pgp-inhibitor:	0.557
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.673
30% Bioavailability (F30%):	0.848

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.774
Plasma Protein Binding (PPB):	92.69294738769531%
Volume Distribution (VD):	0.54
Pgp-substrate:	4.73300313949585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.436
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.623
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	5.744
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.538
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.066
Skin Sensitization:	0.032
Carcinogencity:	0.044
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC163372

Natural Product ID:	NPC163372
*Common Name:**	Antcamphin F
IUPAC Name:	(2R,6R)-6-[(4R,5R,7S,10S,13R,14R,17R)-4,7-dihydroxy-4,10,13-trimethyl-3,11-dioxo-1,2,5,6,7,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
Synonyms:
Standard InCHIKey:	UPCGWWQEYSWYOT-MTBMFYBCSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-15(17(3)26(33)34)7-8-16(2)18-9-10-19-24-20(30)13-22-27(4,12-11-23(32)29(22,6)35)25(24)21(31)14-28(18,19)5/h16-20,22,30,35H,1,7-14H2,2-6H3,(H,33,34)/t16-,17-,18-,19+,20+,22-,27+,28-,29-/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=C(C(=O)C[C@]12C)[C@@]1(C)CCC(=O)[C@@](C)([C@@H]1C[C@@H]3O)O)[C@@H](C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105000
PubChem CID:	76328318
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	66300.0	nM	PMID[518247]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	67200.0	nM	PMID[518247]

☑ 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 NPC163372 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	183
0.1-0.2	1180
0.2-0.3	4645
0.3-0.4	10444
0.4-0.5	11225
0.5-0.6	6791
0.6-0.7	5850
0.7-0.8	2014
0.8-0.85	251
0.85-0.9	93
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC302537
0.9894	High Similarity	NPC119601
0.9894	High Similarity	NPC308726
0.9462	High Similarity	NPC173875
0.9462	High Similarity	NPC469995
0.9462	High Similarity	NPC174948
0.9462	High Similarity	NPC318282
0.9362	High Similarity	NPC328371
0.9362	High Similarity	NPC96859
0.9362	High Similarity	NPC328162
0.9362	High Similarity	NPC305483
0.9271	High Similarity	NPC327431
0.9192	High Similarity	NPC323834
0.9149	High Similarity	NPC166906
0.91	High Similarity	NPC472925
0.9082	High Similarity	NPC204450
0.9082	High Similarity	NPC195290
0.9062	High Similarity	NPC320306
0.9062	High Similarity	NPC43747
0.9062	High Similarity	NPC18319
0.9053	High Similarity	NPC470016
0.9053	High Similarity	NPC317586
0.901	High Similarity	NPC295244
0.899	High Similarity	NPC251017
0.899	High Similarity	NPC236390
0.8969	High Similarity	NPC197386
0.8969	High Similarity	NPC471717
0.8969	High Similarity	NPC10364
0.8958	High Similarity	NPC249954
0.8947	High Similarity	NPC184870
0.8936	High Similarity	NPC63748
0.8925	High Similarity	NPC214387
0.8878	High Similarity	NPC51370
0.8878	High Similarity	NPC287833
0.8878	High Similarity	NPC316964
0.8878	High Similarity	NPC205899
0.8854	High Similarity	NPC37646
0.8854	High Similarity	NPC259286
0.8842	High Similarity	NPC472930
0.8842	High Similarity	NPC69454
0.8835	High Similarity	NPC473036
0.8835	High Similarity	NPC272898
0.883	High Similarity	NPC477147
0.883	High Similarity	NPC469400
0.883	High Similarity	NPC477149
0.8812	High Similarity	NPC51452
0.88	High Similarity	NPC55872
0.8788	High Similarity	NPC472924
0.8763	High Similarity	NPC472941
0.8763	High Similarity	NPC456
0.8763	High Similarity	NPC243525
0.8763	High Similarity	NPC40765
0.8763	High Similarity	NPC3772
0.875	High Similarity	NPC472928
0.8737	High Similarity	NPC107690
0.8725	High Similarity	NPC475294
0.8713	High Similarity	NPC28656
0.87	High Similarity	NPC473424
0.87	High Similarity	NPC56498
0.87	High Similarity	NPC136289
0.8687	High Similarity	NPC476274
0.8687	High Similarity	NPC88198
0.8687	High Similarity	NPC157787
0.8673	High Similarity	NPC106557
0.8673	High Similarity	NPC121339
0.866	High Similarity	NPC472932
0.8646	High Similarity	NPC243866
0.8646	High Similarity	NPC470254
0.8617	High Similarity	NPC143767
0.8617	High Similarity	NPC131470
0.8617	High Similarity	NPC242864
0.8614	High Similarity	NPC111323
0.8614	High Similarity	NPC311612
0.86	High Similarity	NPC476240
0.86	High Similarity	NPC224720
0.86	High Similarity	NPC81530
0.86	High Similarity	NPC476223
0.8586	High Similarity	NPC166745
0.8586	High Similarity	NPC235464
0.8585	High Similarity	NPC472926
0.8571	High Similarity	NPC7124
0.8571	High Similarity	NPC95565
0.8558	High Similarity	NPC77947
0.8558	High Similarity	NPC286174
0.8557	High Similarity	NPC469406
0.8542	High Similarity	NPC168027
0.8542	High Similarity	NPC185936
0.8542	High Similarity	NPC233116
0.8526	High Similarity	NPC86319
0.8526	High Similarity	NPC275740
0.8515	High Similarity	NPC293753
0.8515	High Similarity	NPC234892
0.8515	High Similarity	NPC87351
0.8485	Intermediate Similarity	NPC18509
0.8485	Intermediate Similarity	NPC122294
0.8476	Intermediate Similarity	NPC129689
0.8469	Intermediate Similarity	NPC255809
0.8469	Intermediate Similarity	NPC48330
0.8454	Intermediate Similarity	NPC477436
0.8454	Intermediate Similarity	NPC206810
0.8454	Intermediate Similarity	NPC477435
0.8454	Intermediate Similarity	NPC25750
0.8438	Intermediate Similarity	NPC183283
0.8438	Intermediate Similarity	NPC48010
0.8431	Intermediate Similarity	NPC247957
0.8431	Intermediate Similarity	NPC249187
0.8431	Intermediate Similarity	NPC33973
0.8431	Intermediate Similarity	NPC70967
0.8421	Intermediate Similarity	NPC471722
0.8411	Intermediate Similarity	NPC472929
0.8404	Intermediate Similarity	NPC72133
0.8404	Intermediate Similarity	NPC55309
0.8404	Intermediate Similarity	NPC28252
0.84	Intermediate Similarity	NPC48647
0.84	Intermediate Similarity	NPC114274
0.84	Intermediate Similarity	NPC186810
0.84	Intermediate Similarity	NPC16021
0.8396	Intermediate Similarity	NPC115303
0.8384	Intermediate Similarity	NPC173272
0.8384	Intermediate Similarity	NPC235053
0.8384	Intermediate Similarity	NPC155676
0.8381	Intermediate Similarity	NPC214644
0.8367	Intermediate Similarity	NPC8993
0.8367	Intermediate Similarity	NPC245972
0.8367	Intermediate Similarity	NPC196485
0.8365	Intermediate Similarity	NPC44063
0.8365	Intermediate Similarity	NPC185
0.8365	Intermediate Similarity	NPC473037
0.8365	Intermediate Similarity	NPC475060
0.8365	Intermediate Similarity	NPC220229
0.8364	Intermediate Similarity	NPC472933
0.8351	Intermediate Similarity	NPC473998
0.8351	Intermediate Similarity	NPC23434
0.8351	Intermediate Similarity	NPC475806
0.8351	Intermediate Similarity	NPC99380
0.835	Intermediate Similarity	NPC2436
0.835	Intermediate Similarity	NPC470251
0.835	Intermediate Similarity	NPC216245
0.835	Intermediate Similarity	NPC135854
0.835	Intermediate Similarity	NPC235889
0.835	Intermediate Similarity	NPC72255
0.8349	Intermediate Similarity	NPC472934
0.8349	Intermediate Similarity	NPC471854
0.8349	Intermediate Similarity	NPC472927
0.8333	Intermediate Similarity	NPC54689
0.8333	Intermediate Similarity	NPC474245
0.8333	Intermediate Similarity	NPC123912
0.8333	Intermediate Similarity	NPC155479
0.8333	Intermediate Similarity	NPC477915
0.8333	Intermediate Similarity	NPC309603
0.8333	Intermediate Similarity	NPC473999
0.8318	Intermediate Similarity	NPC221144
0.8318	Intermediate Similarity	NPC475524
0.8318	Intermediate Similarity	NPC100267
0.8317	Intermediate Similarity	NPC154072
0.8317	Intermediate Similarity	NPC241221
0.8317	Intermediate Similarity	NPC144660
0.8317	Intermediate Similarity	NPC144956
0.8317	Intermediate Similarity	NPC307954
0.8317	Intermediate Similarity	NPC299971
0.8316	Intermediate Similarity	NPC187376
0.8316	Intermediate Similarity	NPC159046
0.8316	Intermediate Similarity	NPC233836
0.8316	Intermediate Similarity	NPC136948
0.8302	Intermediate Similarity	NPC37116
0.83	Intermediate Similarity	NPC253826
0.83	Intermediate Similarity	NPC107243
0.83	Intermediate Similarity	NPC108078
0.8298	Intermediate Similarity	NPC474083
0.8286	Intermediate Similarity	NPC217201
0.8286	Intermediate Similarity	NPC65941
0.8283	Intermediate Similarity	NPC476174
0.8283	Intermediate Similarity	NPC271195
0.8283	Intermediate Similarity	NPC200702
0.8283	Intermediate Similarity	NPC477437
0.8283	Intermediate Similarity	NPC134067
0.8283	Intermediate Similarity	NPC241156
0.8283	Intermediate Similarity	NPC477438
0.828	Intermediate Similarity	NPC470015
0.828	Intermediate Similarity	NPC168188
0.8269	Intermediate Similarity	NPC50692
0.8269	Intermediate Similarity	NPC149047
0.8269	Intermediate Similarity	NPC181265
0.8269	Intermediate Similarity	NPC152695
0.8269	Intermediate Similarity	NPC260268
0.8269	Intermediate Similarity	NPC476027
0.8269	Intermediate Similarity	NPC85829
0.8269	Intermediate Similarity	NPC171137
0.8269	Intermediate Similarity	NPC48733
0.8269	Intermediate Similarity	NPC319077
0.8269	Intermediate Similarity	NPC150531
0.8269	Intermediate Similarity	NPC97202
0.8269	Intermediate Similarity	NPC202167
0.8269	Intermediate Similarity	NPC296945
0.8269	Intermediate Similarity	NPC257353
0.8269	Intermediate Similarity	NPC214264
0.8269	Intermediate Similarity	NPC49958
0.8269	Intermediate Similarity	NPC302607
0.8265	Intermediate Similarity	NPC214697
0.8257	Intermediate Similarity	NPC148458

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 NPC163372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1552
0.2-0.3	3859
0.3-0.4	2364
0.4-0.5	724
0.5-0.6	190
0.6-0.7	160
0.7-0.8	111
0.8-0.85	37
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8627	High Similarity	NPD5739	Approved
0.8627	High Similarity	NPD7128	Approved
0.8627	High Similarity	NPD6675	Approved
0.8627	High Similarity	NPD6402	Approved
0.8515	High Similarity	NPD5211	Phase 2
0.8485	Intermediate Similarity	NPD4755	Approved
0.8462	Intermediate Similarity	NPD6881	Approved
0.8462	Intermediate Similarity	NPD6899	Approved
0.8462	Intermediate Similarity	NPD7320	Approved
0.8381	Intermediate Similarity	NPD6373	Approved
0.8381	Intermediate Similarity	NPD6372	Approved
0.8365	Intermediate Similarity	NPD5697	Approved
0.8365	Intermediate Similarity	NPD5701	Approved
0.835	Intermediate Similarity	NPD5141	Approved
0.8333	Intermediate Similarity	NPD5328	Approved
0.8317	Intermediate Similarity	NPD4696	Approved
0.8317	Intermediate Similarity	NPD5286	Approved
0.8317	Intermediate Similarity	NPD5285	Approved
0.8317	Intermediate Similarity	NPD4700	Approved
0.8302	Intermediate Similarity	NPD6883	Approved
0.8302	Intermediate Similarity	NPD7102	Approved
0.8302	Intermediate Similarity	NPD7290	Approved
0.8286	Intermediate Similarity	NPD6011	Approved
0.8235	Intermediate Similarity	NPD5223	Approved
0.8224	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD6650	Approved
0.8224	Intermediate Similarity	NPD8130	Phase 1
0.8224	Intermediate Similarity	NPD6869	Approved
0.8224	Intermediate Similarity	NPD6649	Approved
0.8224	Intermediate Similarity	NPD6617	Approved
0.8224	Intermediate Similarity	NPD6847	Approved
0.8208	Intermediate Similarity	NPD6013	Approved
0.8208	Intermediate Similarity	NPD6012	Approved
0.8208	Intermediate Similarity	NPD6014	Approved
0.82	Intermediate Similarity	NPD5222	Approved
0.82	Intermediate Similarity	NPD5221	Approved
0.82	Intermediate Similarity	NPD4697	Phase 3
0.82	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD6079	Approved
0.8155	Intermediate Similarity	NPD5224	Approved
0.8155	Intermediate Similarity	NPD5226	Approved
0.8155	Intermediate Similarity	NPD4633	Approved
0.8155	Intermediate Similarity	NPD5225	Approved
0.8148	Intermediate Similarity	NPD8297	Approved
0.8148	Intermediate Similarity	NPD6882	Approved
0.8119	Intermediate Similarity	NPD5173	Approved
0.8119	Intermediate Similarity	NPD6084	Phase 2
0.8119	Intermediate Similarity	NPD6083	Phase 2
0.81	Intermediate Similarity	NPD5695	Phase 3
0.8077	Intermediate Similarity	NPD5175	Approved
0.8077	Intermediate Similarity	NPD5174	Approved
0.8077	Intermediate Similarity	NPD4754	Approved
0.8021	Intermediate Similarity	NPD5279	Phase 3
0.7959	Intermediate Similarity	NPD4753	Phase 2
0.7925	Intermediate Similarity	NPD4767	Approved
0.7925	Intermediate Similarity	NPD4768	Approved
0.7909	Intermediate Similarity	NPD4632	Approved
0.79	Intermediate Similarity	NPD4202	Approved
0.79	Intermediate Similarity	NPD6399	Phase 3
0.7857	Intermediate Similarity	NPD6672	Approved
0.7857	Intermediate Similarity	NPD5737	Approved
0.7835	Intermediate Similarity	NPD3618	Phase 1
0.7812	Intermediate Similarity	NPD4786	Approved
0.78	Intermediate Similarity	NPD7515	Phase 2
0.78	Intermediate Similarity	NPD5281	Approved
0.78	Intermediate Similarity	NPD5284	Approved
0.7788	Intermediate Similarity	NPD6335	Approved
0.7778	Intermediate Similarity	NPD5128	Approved
0.7778	Intermediate Similarity	NPD4730	Approved
0.7778	Intermediate Similarity	NPD4729	Approved
0.7768	Intermediate Similarity	NPD6274	Approved
0.7732	Intermediate Similarity	NPD5329	Approved
0.7719	Intermediate Similarity	NPD7100	Approved
0.7719	Intermediate Similarity	NPD7101	Approved
0.7699	Intermediate Similarity	NPD6317	Approved
0.7699	Intermediate Similarity	NPD6009	Approved
0.7699	Intermediate Similarity	NPD7115	Discovery
0.7692	Intermediate Similarity	NPD5696	Approved
0.7653	Intermediate Similarity	NPD5280	Approved
0.7653	Intermediate Similarity	NPD4694	Approved
0.7653	Intermediate Similarity	NPD5690	Phase 2
0.7636	Intermediate Similarity	NPD5251	Approved
0.7636	Intermediate Similarity	NPD5250	Approved
0.7636	Intermediate Similarity	NPD5249	Phase 3
0.7636	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5247	Approved
0.7636	Intermediate Similarity	NPD5169	Approved
0.7636	Intermediate Similarity	NPD5248	Approved
0.7636	Intermediate Similarity	NPD5135	Approved
0.7636	Intermediate Similarity	NPD4634	Approved
0.7632	Intermediate Similarity	NPD6313	Approved
0.7632	Intermediate Similarity	NPD6314	Approved
0.7629	Intermediate Similarity	NPD3666	Approved
0.7629	Intermediate Similarity	NPD4197	Approved
0.7629	Intermediate Similarity	NPD3133	Approved
0.7629	Intermediate Similarity	NPD3665	Phase 1
0.7624	Intermediate Similarity	NPD6050	Approved
0.7619	Intermediate Similarity	NPD7640	Approved
0.7619	Intermediate Similarity	NPD7639	Approved
0.7611	Intermediate Similarity	NPD6868	Approved
0.7604	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD6904	Approved
0.76	Intermediate Similarity	NPD6080	Approved
0.76	Intermediate Similarity	NPD6673	Approved
0.7593	Intermediate Similarity	NPD6008	Approved
0.7586	Intermediate Similarity	NPD6909	Approved
0.7586	Intermediate Similarity	NPD6908	Approved
0.7573	Intermediate Similarity	NPD5210	Approved
0.7573	Intermediate Similarity	NPD4629	Approved
0.7568	Intermediate Similarity	NPD5215	Approved
0.7568	Intermediate Similarity	NPD5217	Approved
0.7568	Intermediate Similarity	NPD5127	Approved
0.7568	Intermediate Similarity	NPD5216	Approved
0.7551	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5692	Phase 3
0.7524	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.7476	Intermediate Similarity	NPD7748	Approved
0.7475	Intermediate Similarity	NPD7146	Approved
0.7475	Intermediate Similarity	NPD7521	Approved
0.7475	Intermediate Similarity	NPD7334	Approved
0.7475	Intermediate Similarity	NPD6409	Approved
0.7475	Intermediate Similarity	NPD6684	Approved
0.7475	Intermediate Similarity	NPD5330	Approved
0.7458	Intermediate Similarity	NPD7604	Phase 2
0.7455	Intermediate Similarity	NPD5168	Approved
0.7451	Intermediate Similarity	NPD5693	Phase 1
0.7451	Intermediate Similarity	NPD5694	Approved
0.7436	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5983	Phase 2
0.7429	Intermediate Similarity	NPD7902	Approved
0.7426	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4223	Phase 3
0.7423	Intermediate Similarity	NPD4221	Approved
0.7404	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD7492	Approved
0.7368	Intermediate Similarity	NPD3617	Approved
0.7368	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5167	Approved
0.735	Intermediate Similarity	NPD6054	Approved
0.735	Intermediate Similarity	NPD6059	Approved
0.7345	Intermediate Similarity	NPD6053	Discontinued
0.7333	Intermediate Similarity	NPD6336	Discontinued
0.7333	Intermediate Similarity	NPD6616	Approved
0.7327	Intermediate Similarity	NPD6903	Approved
0.7327	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6098	Approved
0.73	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8035	Phase 2
0.7282	Intermediate Similarity	NPD8034	Phase 2
0.7282	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD8293	Discontinued
0.7227	Intermediate Similarity	NPD6370	Approved
0.7216	Intermediate Similarity	NPD7525	Registered
0.7216	Intermediate Similarity	NPD4695	Discontinued
0.7213	Intermediate Similarity	NPD7736	Approved
0.7212	Intermediate Similarity	NPD5779	Approved
0.7212	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD4788	Approved
0.7156	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6404	Discontinued
0.7129	Intermediate Similarity	NPD4138	Approved
0.7129	Intermediate Similarity	NPD4693	Phase 3
0.7129	Intermediate Similarity	NPD5205	Approved
0.7129	Intermediate Similarity	NPD4623	Approved
0.7129	Intermediate Similarity	NPD4690	Approved
0.7129	Intermediate Similarity	NPD4519	Discontinued
0.7129	Intermediate Similarity	NPD4688	Approved
0.7129	Intermediate Similarity	NPD4689	Approved
0.71	Intermediate Similarity	NPD3668	Phase 3
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6116	Phase 1
0.7083	Intermediate Similarity	NPD5988	Approved
0.7075	Intermediate Similarity	NPD5654	Approved
0.7059	Intermediate Similarity	NPD3573	Approved
0.7049	Intermediate Similarity	NPD7507	Approved
0.7048	Intermediate Similarity	NPD5133	Approved
0.703	Intermediate Similarity	NPD1696	Phase 3
0.703	Intermediate Similarity	NPD5363	Approved
0.7019	Intermediate Similarity	NPD5785	Approved
0.7019	Intermediate Similarity	NPD5207	Approved
0.7	Intermediate Similarity	NPD5362	Discontinued
0.699	Remote Similarity	NPD5208	Approved
0.6981	Remote Similarity	NPD6001	Approved
0.6979	Remote Similarity	NPD6117	Approved
0.697	Remote Similarity	NPD4139	Approved
0.697	Remote Similarity	NPD4692	Approved
0.6961	Remote Similarity	NPD5786	Approved
0.6944	Remote Similarity	NPD5959	Approved
0.6935	Remote Similarity	NPD6033	Approved
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7260	Phase 2
0.6903	Remote Similarity	NPD6412	Phase 2
0.69	Remote Similarity	NPD4269	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