NPASS Compound

Structure

NPC200702 OpenBabel07101719252D 37 40 0 0 1 0 0 0 0 0999 V2000 -4.1712 3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5402 3.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6984 -3.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9552 -4.4677 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 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2308 -3.6974 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 1 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 -0.7473 -3.4895 0.0000 C 0 0 0 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 -0.0000 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 2 0 0 0 0 0 0 0 0 0 2.5472 -2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 -4.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0563 -2.5385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 29 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 31 1 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 17 30 1 6 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 24 1 0 0 0 0 19 32 2 0 0 0 0 20 25 1 0 0 0 0 20 33 1 1 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 0 0 0 0 22 34 1 1 0 0 0 23 30 1 1 0 0 0 23 35 1 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 27 37 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.36
Volume:	549.469
LogP:	2.726
LogD:	2.216
LogS:	-3.603
# Rotatable Bonds:	6
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.442
Fsp3:	0.9
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.264
MDCK Permeability:	4.495308985497104e-06
Pgp-inhibitor:	0.322
Pgp-substrate:	0.271
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.858

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	83.93115997314453%
Volume Distribution (VD):	0.528
Pgp-substrate:	8.611515045166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.337

ADMET: Excretion

Clearance (CL):	2.586
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.418
Carcinogencity:	0.007
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC200702

Natural Product ID:	NPC200702
*Common Name:**	Fasciculol M
IUPAC Name:	(2R,3R,5R,10S,12S,13R,14R,17R)-2,3,12-trihydroxy-4,4,10,13,14-pentamethyl-17-[(2R,5R)-1,5,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
Synonyms:
Standard InCHIKey:	FVNOMENBXLRMPE-YZPVWUHISA-N
Standard InCHI:	InChI=1S/C30H50O7/c1-26(2)21-13-19(32)24-18(28(21,5)14-20(33)25(26)36)12-23(35)30(7)17(10-11-29(24,30)6)16(15-31)8-9-22(34)27(3,4)37/h16-17,20-23,25,31,33-37H,8-15H2,1-7H3/t16-,17+,20+,21-,22+,23-,25-,28+,29-,30-/m0/s1
SMILES:	OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)[C@@H](O)CC1=C2C(=O)C[C@@H]2[C@]1(C)C[C@@H](O)[C@@H](C2(C)C)O)C)CC[C@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375633
PubChem CID:	71712506
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
NPO33351	naematoloma fasciculare	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23634786]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	49900.0	nM	PMID[481699]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	8500.0	nM	PMID[481699]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	7360.0	nM	PMID[481699]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	4770.0	nM	PMID[481699]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3990.0	nM	PMID[481699]

☑ 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 NPC200702 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	202
0.1-0.2	1489
0.2-0.3	5278
0.3-0.4	12052
0.4-0.5	10013
0.5-0.6	6787
0.6-0.7	5332
0.7-0.8	1344
0.8-0.85	148
0.85-0.9	44
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC136801
0.9205	High Similarity	NPC138756
0.9149	High Similarity	NPC316964
0.9072	High Similarity	NPC323834
0.8901	High Similarity	NPC289213
0.8889	High Similarity	NPC143767
0.8889	High Similarity	NPC131470
0.8878	High Similarity	NPC149047
0.8817	High Similarity	NPC166906
0.8791	High Similarity	NPC86319
0.8791	High Similarity	NPC77263
0.8791	High Similarity	NPC275740
0.8791	High Similarity	NPC250592
0.8788	High Similarity	NPC475060
0.8788	High Similarity	NPC220229
0.8778	High Similarity	NPC99909
0.8776	High Similarity	NPC204833
0.8776	High Similarity	NPC209502
0.8763	High Similarity	NPC473424
0.8723	High Similarity	NPC470016
0.8723	High Similarity	NPC317586
0.8723	High Similarity	NPC473170
0.87	High Similarity	NPC217201
0.87	High Similarity	NPC65941
0.8696	High Similarity	NPC183283
0.8687	High Similarity	NPC97202
0.8687	High Similarity	NPC214264
0.8687	High Similarity	NPC202167
0.8687	High Similarity	NPC296945
0.8687	High Similarity	NPC150531
0.8687	High Similarity	NPC50692
0.8687	High Similarity	NPC49958
0.8687	High Similarity	NPC302607
0.8687	High Similarity	NPC260268
0.8687	High Similarity	NPC171137
0.8687	High Similarity	NPC152695
0.8687	High Similarity	NPC48733
0.8687	High Similarity	NPC85829
0.8687	High Similarity	NPC319077
0.8687	High Similarity	NPC476027
0.8681	High Similarity	NPC471722
0.8673	High Similarity	NPC191892
0.8667	High Similarity	NPC72133
0.8636	High Similarity	NPC7988
0.8632	High Similarity	NPC328162
0.8632	High Similarity	NPC95565
0.8632	High Similarity	NPC305483
0.8632	High Similarity	NPC96859
0.8632	High Similarity	NPC249954
0.8617	High Similarity	NPC196485
0.8617	High Similarity	NPC245972
0.8614	High Similarity	NPC11710
0.8602	High Similarity	NPC233116
0.8602	High Similarity	NPC155304
0.8602	High Similarity	NPC63748
0.86	High Similarity	NPC83744
0.86	High Similarity	NPC477916
0.8587	High Similarity	NPC186688
0.8587	High Similarity	NPC32830
0.8571	High Similarity	NPC477915
0.8556	High Similarity	NPC197823
0.8542	High Similarity	NPC320306
0.8526	High Similarity	NPC297199
0.8526	High Similarity	NPC48330
0.8526	High Similarity	NPC255809
0.8526	High Similarity	NPC259286
0.8515	High Similarity	NPC329417
0.8511	High Similarity	NPC69454
0.8485	Intermediate Similarity	NPC55872
0.8485	Intermediate Similarity	NPC251017
0.8478	Intermediate Similarity	NPC328539
0.8454	Intermediate Similarity	NPC114274
0.8438	Intermediate Similarity	NPC173272
0.8438	Intermediate Similarity	NPC471463
0.8438	Intermediate Similarity	NPC7124
0.8421	Intermediate Similarity	NPC111015
0.8416	Intermediate Similarity	NPC165873
0.8409	Intermediate Similarity	NPC22403
0.8404	Intermediate Similarity	NPC73457
0.8404	Intermediate Similarity	NPC185936
0.8404	Intermediate Similarity	NPC168027
0.84	Intermediate Similarity	NPC28656
0.8387	Intermediate Similarity	NPC31985
0.8387	Intermediate Similarity	NPC1015
0.837	Intermediate Similarity	NPC241875
0.837	Intermediate Similarity	NPC469314
0.837	Intermediate Similarity	NPC469317
0.837	Intermediate Similarity	NPC475740
0.8367	Intermediate Similarity	NPC327431
0.8367	Intermediate Similarity	NPC157787
0.8367	Intermediate Similarity	NPC110149
0.8367	Intermediate Similarity	NPC88198
0.8351	Intermediate Similarity	NPC170978
0.8351	Intermediate Similarity	NPC190554
0.8351	Intermediate Similarity	NPC108078
0.8351	Intermediate Similarity	NPC43747
0.8351	Intermediate Similarity	NPC122294
0.835	Intermediate Similarity	NPC76084
0.8333	Intermediate Similarity	NPC174948
0.8333	Intermediate Similarity	NPC271195
0.8333	Intermediate Similarity	NPC318282
0.8333	Intermediate Similarity	NPC173875
0.8333	Intermediate Similarity	NPC127063
0.8333	Intermediate Similarity	NPC469995
0.8317	Intermediate Similarity	NPC51452
0.8316	Intermediate Similarity	NPC472930
0.8316	Intermediate Similarity	NPC25750
0.8316	Intermediate Similarity	NPC206810
0.8298	Intermediate Similarity	NPC191684
0.8286	Intermediate Similarity	NPC73300
0.8286	Intermediate Similarity	NPC108721
0.8283	Intermediate Similarity	NPC302537
0.8283	Intermediate Similarity	NPC163372
0.828	Intermediate Similarity	NPC193360
0.828	Intermediate Similarity	NPC44181
0.828	Intermediate Similarity	NPC53911
0.828	Intermediate Similarity	NPC242864
0.828	Intermediate Similarity	NPC471724
0.8265	Intermediate Similarity	NPC16021
0.8261	Intermediate Similarity	NPC474732
0.8261	Intermediate Similarity	NPC474733
0.8261	Intermediate Similarity	NPC222613
0.8261	Intermediate Similarity	NPC474778
0.8261	Intermediate Similarity	NPC31564
0.8261	Intermediate Similarity	NPC118648
0.8261	Intermediate Similarity	NPC145879
0.8261	Intermediate Similarity	NPC475022
0.8261	Intermediate Similarity	NPC89077
0.8252	Intermediate Similarity	NPC214644
0.8247	Intermediate Similarity	NPC117133
0.8247	Intermediate Similarity	NPC328371
0.8242	Intermediate Similarity	NPC473246
0.8235	Intermediate Similarity	NPC472925
0.8235	Intermediate Similarity	NPC473037
0.8229	Intermediate Similarity	NPC472976
0.8229	Intermediate Similarity	NPC318332
0.8229	Intermediate Similarity	NPC184870
0.8229	Intermediate Similarity	NPC472977
0.8229	Intermediate Similarity	NPC196227
0.8218	Intermediate Similarity	NPC477812
0.8211	Intermediate Similarity	NPC19114
0.8211	Intermediate Similarity	NPC189520
0.8211	Intermediate Similarity	NPC116726
0.82	Intermediate Similarity	NPC119601
0.82	Intermediate Similarity	NPC308726
0.8191	Intermediate Similarity	NPC474245
0.819	Intermediate Similarity	NPC207251
0.8182	Intermediate Similarity	NPC144660
0.8182	Intermediate Similarity	NPC307954
0.8182	Intermediate Similarity	NPC299971
0.8182	Intermediate Similarity	NPC83709
0.8182	Intermediate Similarity	NPC474720
0.8182	Intermediate Similarity	NPC15390
0.8182	Intermediate Similarity	NPC154072
0.8173	Intermediate Similarity	NPC473036
0.8173	Intermediate Similarity	NPC272898
0.8173	Intermediate Similarity	NPC5284
0.8172	Intermediate Similarity	NPC90652
0.8172	Intermediate Similarity	NPC58063
0.8163	Intermediate Similarity	NPC18509
0.8163	Intermediate Similarity	NPC161147
0.8163	Intermediate Similarity	NPC18319
0.8152	Intermediate Similarity	NPC469948
0.8152	Intermediate Similarity	NPC470574
0.8144	Intermediate Similarity	NPC472824
0.8144	Intermediate Similarity	NPC241156
0.8144	Intermediate Similarity	NPC472932
0.8144	Intermediate Similarity	NPC472485
0.8144	Intermediate Similarity	NPC37646
0.8137	Intermediate Similarity	NPC166607
0.8132	Intermediate Similarity	NPC476082
0.8132	Intermediate Similarity	NPC66764
0.8132	Intermediate Similarity	NPC278648
0.8132	Intermediate Similarity	NPC110150
0.8125	Intermediate Similarity	NPC475255
0.8125	Intermediate Similarity	NPC109305
0.8119	Intermediate Similarity	NPC471005
0.8119	Intermediate Similarity	NPC33973
0.8119	Intermediate Similarity	NPC70967
0.8119	Intermediate Similarity	NPC264048
0.8119	Intermediate Similarity	NPC247957
0.8119	Intermediate Similarity	NPC218513
0.8119	Intermediate Similarity	NPC249187
0.8119	Intermediate Similarity	NPC55954
0.8113	Intermediate Similarity	NPC317210
0.8113	Intermediate Similarity	NPC250109
0.8113	Intermediate Similarity	NPC962
0.8105	Intermediate Similarity	NPC48010
0.8105	Intermediate Similarity	NPC20388
0.8105	Intermediate Similarity	NPC469400
0.81	Intermediate Similarity	NPC472924
0.8085	Intermediate Similarity	NPC158778
0.8085	Intermediate Similarity	NPC470417
0.8081	Intermediate Similarity	NPC477854
0.8081	Intermediate Similarity	NPC10364
0.8077	Intermediate Similarity	NPC286174
0.8077	Intermediate Similarity	NPC77947
0.8065	Intermediate Similarity	NPC28252
0.8065	Intermediate Similarity	NPC94755
0.8065	Intermediate Similarity	NPC472491

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 NPC200702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1992
0.2-0.3	4065
0.3-0.4	1992
0.4-0.5	487
0.5-0.6	153
0.6-0.7	168
0.7-0.8	110
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
0.8587	High Similarity	NPD5328	Approved
0.8404	Intermediate Similarity	NPD6079	Approved
0.8163	Intermediate Similarity	NPD4755	Approved
0.8065	Intermediate Similarity	NPD3618	Phase 1
0.8061	Intermediate Similarity	NPD5222	Approved
0.8061	Intermediate Similarity	NPD5221	Approved
0.8061	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4697	Phase 3
0.8043	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD4700	Approved
0.8	Intermediate Similarity	NPD4634	Approved
0.8	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD5285	Approved
0.798	Intermediate Similarity	NPD5173	Approved
0.7938	Intermediate Similarity	NPD4202	Approved
0.7921	Intermediate Similarity	NPD5223	Approved
0.7843	Intermediate Similarity	NPD5226	Approved
0.7843	Intermediate Similarity	NPD5211	Phase 2
0.7843	Intermediate Similarity	NPD5224	Approved
0.7843	Intermediate Similarity	NPD5225	Approved
0.7843	Intermediate Similarity	NPD4633	Approved
0.7826	Intermediate Similarity	NPD3667	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD4632	Approved
0.7767	Intermediate Similarity	NPD4754	Approved
0.7767	Intermediate Similarity	NPD5175	Approved
0.7767	Intermediate Similarity	NPD5174	Approved
0.7692	Intermediate Similarity	NPD5141	Approved
0.7684	Intermediate Similarity	NPD5279	Phase 3
0.766	Intermediate Similarity	NPD3133	Approved
0.766	Intermediate Similarity	NPD3665	Phase 1
0.766	Intermediate Similarity	NPD3666	Approved
0.7642	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6881	Approved
0.7629	Intermediate Similarity	NPD4753	Phase 2
0.7619	Intermediate Similarity	NPD4767	Approved
0.7619	Intermediate Similarity	NPD4768	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD6373	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7547	Intermediate Similarity	NPD5697	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD4729	Approved
0.7477	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD4730	Approved
0.7475	Intermediate Similarity	NPD7515	Phase 2
0.7453	Intermediate Similarity	NPD6008	Approved
0.7447	Intermediate Similarity	NPD4221	Approved
0.7447	Intermediate Similarity	NPD4223	Phase 3
0.7444	Intermediate Similarity	NPD3703	Phase 2
0.7431	Intermediate Similarity	NPD6617	Approved
0.7431	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6869	Approved
0.7431	Intermediate Similarity	NPD6649	Approved
0.7431	Intermediate Similarity	NPD6847	Approved
0.7431	Intermediate Similarity	NPD8130	Phase 1
0.7431	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6009	Approved
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD6014	Approved
0.74	Intermediate Similarity	NPD6399	Phase 3
0.7396	Intermediate Similarity	NPD5329	Approved
0.7391	Intermediate Similarity	NPD3617	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6059	Approved
0.7368	Intermediate Similarity	NPD6319	Approved
0.7364	Intermediate Similarity	NPD6882	Approved
0.734	Intermediate Similarity	NPD4139	Approved
0.734	Intermediate Similarity	NPD4692	Approved
0.7339	Intermediate Similarity	NPD5135	Approved
0.7339	Intermediate Similarity	NPD5251	Approved
0.7339	Intermediate Similarity	NPD5249	Phase 3
0.7339	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5250	Approved
0.7339	Intermediate Similarity	NPD5169	Approved
0.7339	Intermediate Similarity	NPD5247	Approved
0.7339	Intermediate Similarity	NPD5248	Approved
0.732	Intermediate Similarity	NPD5690	Phase 2
0.732	Intermediate Similarity	NPD5280	Approved
0.732	Intermediate Similarity	NPD4694	Approved
0.7315	Intermediate Similarity	NPD5168	Approved
0.7292	Intermediate Similarity	NPD4197	Approved
0.7292	Intermediate Similarity	NPD3668	Phase 3
0.7282	Intermediate Similarity	NPD6083	Phase 2
0.7282	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD5215	Approved
0.7273	Intermediate Similarity	NPD5127	Approved
0.7273	Intermediate Similarity	NPD5216	Approved
0.7257	Intermediate Similarity	NPD7115	Discovery
0.7255	Intermediate Similarity	NPD5695	Phase 3
0.7255	Intermediate Similarity	NPD4629	Approved
0.7255	Intermediate Similarity	NPD5210	Approved
0.7248	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6370	Approved
0.7234	Intermediate Similarity	NPD4748	Discontinued
0.7234	Intermediate Similarity	NPD7525	Registered
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7216	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7638	Approved
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7204	Intermediate Similarity	NPD6697	Approved
0.7204	Intermediate Similarity	NPD6118	Approved
0.7188	Intermediate Similarity	NPD4788	Approved
0.7179	Intermediate Similarity	NPD7604	Phase 2
0.7157	Intermediate Similarity	NPD7748	Approved
0.7155	Intermediate Similarity	NPD5983	Phase 2
0.7155	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD4688	Approved
0.7129	Intermediate Similarity	NPD5284	Approved
0.7129	Intermediate Similarity	NPD5281	Approved
0.7119	Intermediate Similarity	NPD7492	Approved
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5988	Approved
0.7091	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5167	Approved
0.7065	Intermediate Similarity	NPD6942	Approved
0.7065	Intermediate Similarity	NPD7339	Approved
0.7059	Intermediate Similarity	NPD6616	Approved
0.7059	Intermediate Similarity	NPD6336	Discontinued
0.7043	Intermediate Similarity	NPD6335	Approved
0.7018	Intermediate Similarity	NPD6274	Approved
0.7018	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.7	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD8293	Discontinued
0.6989	Remote Similarity	NPD6117	Approved
0.6983	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD7100	Approved
0.697	Remote Similarity	NPD5330	Approved
0.697	Remote Similarity	NPD7146	Approved
0.697	Remote Similarity	NPD7521	Approved
0.697	Remote Similarity	NPD6409	Approved
0.697	Remote Similarity	NPD6684	Approved
0.697	Remote Similarity	NPD7334	Approved
0.6957	Remote Similarity	NPD6317	Approved
0.6952	Remote Similarity	NPD7902	Approved
0.6942	Remote Similarity	NPD6033	Approved
0.6942	Remote Similarity	NPD7736	Approved
0.6923	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7507	Approved
0.6915	Remote Similarity	NPD6116	Phase 1
0.6897	Remote Similarity	NPD6314	Approved
0.6897	Remote Similarity	NPD6313	Approved
0.6893	Remote Similarity	NPD5133	Approved
0.6889	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5696	Approved
0.6875	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4695	Discontinued
0.6864	Remote Similarity	NPD6909	Approved
0.6864	Remote Similarity	NPD6908	Approved
0.6863	Remote Similarity	NPD4096	Approved
0.6832	Remote Similarity	NPD4518	Approved
0.6832	Remote Similarity	NPD6903	Approved
0.6832	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7341	Phase 2
0.6809	Remote Similarity	NPD6933	Approved
0.6809	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8034	Phase 2
0.6796	Remote Similarity	NPD6411	Approved
0.6796	Remote Similarity	NPD6050	Approved
0.6796	Remote Similarity	NPD8035	Phase 2
0.6778	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5360	Phase 3
0.6774	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5733	Approved
0.6771	Remote Similarity	NPD4195	Approved
0.6765	Remote Similarity	NPD6673	Approved
0.6765	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6080	Approved
0.6765	Remote Similarity	NPD6904	Approved
0.6754	Remote Similarity	NPD6053	Discontinued
0.6748	Remote Similarity	NPD7319	Approved
0.6733	Remote Similarity	NPD7524	Approved
0.6733	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3573	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