NPASS Compound

Structure

CID280556 OpenBabel06191716092D 36 39 0 0 1 0 0 0 0 0999 V2000 -3.3806 3.9367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2560 3.4311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7630 -4.2252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9742 -4.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5352 0.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2727 -2.2510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 2.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6909 2.9260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6694 -3.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3797 0.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8148 -1.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 -0.4876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6903 0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2243 1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5357 2.4379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0968 -3.9301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2246 2.4374 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3803 2.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8726 -3.8285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 1.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9751 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 2.2115 -2.4542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0903 0.9616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4935 -4.8204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -1.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0908 2.9371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2693 -2.9381 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 11 1 0 0 0 0 9 10 1 0 0 0 0 9 19 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 29 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 18 30 1 6 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 1 0 0 0 22 26 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 0 0 0 0 23 33 1 1 0 0 0 24 30 1 1 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 35 1 6 0 0 0 27 36 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:	506.36
Volume:	540.679
LogP:	3.3
LogD:	2.892
LogS:	-3.741
# Rotatable Bonds:	6
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	5.526
Fsp3:	0.867
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:	-5.151
MDCK Permeability:	3.902320258930558e-06
Pgp-inhibitor:	0.946
Pgp-substrate:	0.366
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.369

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	87.18436431884766%
Volume Distribution (VD):	0.618
Pgp-substrate:	8.329263687133789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	2.972
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.696
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.955
Carcinogencity:	0.209
Eye Corrosion:	0.004
Eye Irritation:	0.04
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC280556

Natural Product ID:	NPC280556
*Common Name:**	Sublateriol C
IUPAC Name:	(2R,3R,5R,10S,12S,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R,5R)-1,5,6-trihydroxy-6-methylheptan-2-yl]-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-2,3,12-triol
Synonyms:
Standard InCHIKey:	LLGNEUSXABUCAV-YTOKZNHUSA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-26(2)22-10-9-19-20(28(22,5)15-21(32)25(26)35)14-24(34)30(7)18(12-13-29(19,30)6)17(16-31)8-11-23(33)27(3,4)36/h9,14,17-18,21-25,31-36H,8,10-13,15-16H2,1-7H3/t17-,18+,21+,22-,23+,24-,25-,28+,29-,30-/m0/s1
SMILES:	OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)[C@@H](O)C=C1C2=CC[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:	CHEMBL2375644
PubChem CID:	10696940
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]
NPO18771	Hypholoma sublateritium	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18771	Hypholoma sublateritium	Species	Strophariaceae	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	7710.0	nM	PMID[568420]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	4540.0	nM	PMID[568420]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4470.0	nM	PMID[568420]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	3290.0	nM	PMID[568420]

☑ 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 NPC280556 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	170
0.1-0.2	1316
0.2-0.3	4963
0.3-0.4	13807
0.4-0.5	10717
0.5-0.6	6842
0.6-0.7	3905
0.7-0.8	886
0.8-0.85	72
0.85-0.9	13
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC6707
0.9091	High Similarity	NPC310013
0.907	High Similarity	NPC474668
0.907	High Similarity	NPC133588
0.9048	High Similarity	NPC231310
0.9036	High Similarity	NPC202389
0.9036	High Similarity	NPC7988
0.8837	High Similarity	NPC6391
0.8837	High Similarity	NPC261266
0.8824	High Similarity	NPC238485
0.881	High Similarity	NPC87489
0.8795	High Similarity	NPC22403
0.8764	High Similarity	NPC41554
0.8764	High Similarity	NPC97404
0.875	High Similarity	NPC470361
0.8706	High Similarity	NPC474634
0.8706	High Similarity	NPC317458
0.8652	High Similarity	NPC11216
0.8652	High Similarity	NPC80561
0.8652	High Similarity	NPC329596
0.8652	High Similarity	NPC204188
0.8652	High Similarity	NPC291484
0.8652	High Similarity	NPC3345
0.8621	High Similarity	NPC94462
0.8605	High Similarity	NPC185568
0.8588	High Similarity	NPC30166
0.8587	High Similarity	NPC72204
0.8571	High Similarity	NPC236112
0.8556	High Similarity	NPC275671
0.8554	High Similarity	NPC205455
0.8554	High Similarity	NPC186191
0.8523	High Similarity	NPC470620
0.8506	High Similarity	NPC470360
0.8488	Intermediate Similarity	NPC207013
0.8488	Intermediate Similarity	NPC470384
0.8471	Intermediate Similarity	NPC474531
0.8471	Intermediate Similarity	NPC23852
0.8471	Intermediate Similarity	NPC209620
0.8452	Intermediate Similarity	NPC30986
0.8452	Intermediate Similarity	NPC209430
0.8444	Intermediate Similarity	NPC107189
0.8444	Intermediate Similarity	NPC295668
0.8434	Intermediate Similarity	NPC214570
0.8427	Intermediate Similarity	NPC470542
0.8409	Intermediate Similarity	NPC293287
0.8409	Intermediate Similarity	NPC299068
0.8409	Intermediate Similarity	NPC152808
0.8391	Intermediate Similarity	NPC205845
0.8387	Intermediate Similarity	NPC288970
0.8372	Intermediate Similarity	NPC49964
0.8372	Intermediate Similarity	NPC101462
0.8372	Intermediate Similarity	NPC296701
0.8372	Intermediate Similarity	NPC218616
0.8372	Intermediate Similarity	NPC20853
0.8372	Intermediate Similarity	NPC201852
0.8372	Intermediate Similarity	NPC50964
0.837	Intermediate Similarity	NPC477605
0.8353	Intermediate Similarity	NPC13554
0.8333	Intermediate Similarity	NPC105495
0.8333	Intermediate Similarity	NPC318136
0.8333	Intermediate Similarity	NPC477606
0.8333	Intermediate Similarity	NPC275910
0.8315	Intermediate Similarity	NPC271967
0.8313	Intermediate Similarity	NPC73875
0.8313	Intermediate Similarity	NPC202642
0.8313	Intermediate Similarity	NPC46160
0.8298	Intermediate Similarity	NPC261807
0.8295	Intermediate Similarity	NPC318390
0.8276	Intermediate Similarity	NPC320548
0.8261	Intermediate Similarity	NPC137461
0.8261	Intermediate Similarity	NPC214697
0.8256	Intermediate Similarity	NPC264245
0.8242	Intermediate Similarity	NPC470390
0.8242	Intermediate Similarity	NPC245410
0.8242	Intermediate Similarity	NPC136801
0.8242	Intermediate Similarity	NPC192437
0.8242	Intermediate Similarity	NPC270511
0.8235	Intermediate Similarity	NPC109546
0.8235	Intermediate Similarity	NPC143182
0.8235	Intermediate Similarity	NPC328714
0.8235	Intermediate Similarity	NPC28862
0.8235	Intermediate Similarity	NPC47982
0.8235	Intermediate Similarity	NPC84694
0.8235	Intermediate Similarity	NPC81306
0.8222	Intermediate Similarity	NPC2158
0.8222	Intermediate Similarity	NPC67872
0.8202	Intermediate Similarity	NPC139724
0.8202	Intermediate Similarity	NPC71520
0.8202	Intermediate Similarity	NPC269058
0.8193	Intermediate Similarity	NPC322353
0.8193	Intermediate Similarity	NPC121744
0.8193	Intermediate Similarity	NPC118508
0.8182	Intermediate Similarity	NPC124172
0.8182	Intermediate Similarity	NPC470077
0.8182	Intermediate Similarity	NPC474047
0.8182	Intermediate Similarity	NPC474493
0.8172	Intermediate Similarity	NPC469406
0.8172	Intermediate Similarity	NPC127718
0.8172	Intermediate Similarity	NPC474922
0.8172	Intermediate Similarity	NPC65402
0.8171	Intermediate Similarity	NPC201373
0.8161	Intermediate Similarity	NPC470049
0.8152	Intermediate Similarity	NPC212948
0.8152	Intermediate Similarity	NPC210268
0.814	Intermediate Similarity	NPC102253
0.814	Intermediate Similarity	NPC209944
0.814	Intermediate Similarity	NPC234193
0.814	Intermediate Similarity	NPC322313
0.814	Intermediate Similarity	NPC241290
0.814	Intermediate Similarity	NPC236237
0.814	Intermediate Similarity	NPC164840
0.8132	Intermediate Similarity	NPC259875
0.8132	Intermediate Similarity	NPC109744
0.8132	Intermediate Similarity	NPC187785
0.8118	Intermediate Similarity	NPC285761
0.8118	Intermediate Similarity	NPC87604
0.8118	Intermediate Similarity	NPC474216
0.8111	Intermediate Similarity	NPC476948
0.8111	Intermediate Similarity	NPC149224
0.8111	Intermediate Similarity	NPC138756
0.8111	Intermediate Similarity	NPC186145
0.8111	Intermediate Similarity	NPC474657
0.8105	Intermediate Similarity	NPC99726
0.8105	Intermediate Similarity	NPC476893
0.8105	Intermediate Similarity	NPC477226
0.8095	Intermediate Similarity	NPC189883
0.8095	Intermediate Similarity	NPC247325
0.8095	Intermediate Similarity	NPC470362
0.8095	Intermediate Similarity	NPC244488
0.809	Intermediate Similarity	NPC266511
0.809	Intermediate Similarity	NPC274448
0.8085	Intermediate Similarity	NPC8774
0.8085	Intermediate Similarity	NPC476894
0.8068	Intermediate Similarity	NPC475789
0.8068	Intermediate Similarity	NPC110778
0.8068	Intermediate Similarity	NPC85095
0.8068	Intermediate Similarity	NPC132635
0.8068	Intermediate Similarity	NPC82623
0.8068	Intermediate Similarity	NPC211135
0.8068	Intermediate Similarity	NPC216420
0.8065	Intermediate Similarity	NPC27918
0.8046	Intermediate Similarity	NPC476646
0.8046	Intermediate Similarity	NPC47761
0.8046	Intermediate Similarity	NPC249423
0.8046	Intermediate Similarity	NPC470383
0.8046	Intermediate Similarity	NPC320525
0.8043	Intermediate Similarity	NPC475751
0.8043	Intermediate Similarity	NPC14380
0.8043	Intermediate Similarity	NPC473956
0.8023	Intermediate Similarity	NPC1319
0.8023	Intermediate Similarity	NPC80530
0.8023	Intermediate Similarity	NPC273410
0.8022	Intermediate Similarity	NPC44181
0.8022	Intermediate Similarity	NPC475605
0.8022	Intermediate Similarity	NPC475664
0.8021	Intermediate Similarity	NPC476895
0.8	Intermediate Similarity	NPC470758
0.8	Intermediate Similarity	NPC470711
0.8	Intermediate Similarity	NPC210717
0.8	Intermediate Similarity	NPC24277
0.8	Intermediate Similarity	NPC318495
0.8	Intermediate Similarity	NPC201273
0.8	Intermediate Similarity	NPC227583
0.8	Intermediate Similarity	NPC125399
0.8	Intermediate Similarity	NPC155986
0.8	Intermediate Similarity	NPC89077
0.8	Intermediate Similarity	NPC98457
0.8	Intermediate Similarity	NPC198968
0.8	Intermediate Similarity	NPC103165
0.8	Intermediate Similarity	NPC130136
0.8	Intermediate Similarity	NPC477604
0.8	Intermediate Similarity	NPC12103
0.798	Intermediate Similarity	NPC204833
0.798	Intermediate Similarity	NPC209502
0.7979	Intermediate Similarity	NPC144202
0.7979	Intermediate Similarity	NPC119562
0.7979	Intermediate Similarity	NPC279410
0.7978	Intermediate Similarity	NPC209802
0.7978	Intermediate Similarity	NPC15534
0.7976	Intermediate Similarity	NPC257347
0.7976	Intermediate Similarity	NPC32832
0.7976	Intermediate Similarity	NPC471723
0.7976	Intermediate Similarity	NPC141071
0.7959	Intermediate Similarity	NPC22634
0.7957	Intermediate Similarity	NPC471453
0.7957	Intermediate Similarity	NPC233116
0.7957	Intermediate Similarity	NPC114389
0.7955	Intermediate Similarity	NPC1272
0.7955	Intermediate Similarity	NPC189972
0.7955	Intermediate Similarity	NPC248886
0.7955	Intermediate Similarity	NPC471408
0.7955	Intermediate Similarity	NPC470614
0.7952	Intermediate Similarity	NPC130665
0.7935	Intermediate Similarity	NPC101886
0.7935	Intermediate Similarity	NPC138974
0.7935	Intermediate Similarity	NPC16265
0.7931	Intermediate Similarity	NPC96362
0.7931	Intermediate Similarity	NPC26117
0.7931	Intermediate Similarity	NPC324772
0.7931	Intermediate Similarity	NPC287749

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 NPC280556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1564
0.2-0.3	4209
0.3-0.4	2258
0.4-0.5	547
0.5-0.6	225
0.6-0.7	159
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.814	Intermediate Similarity	NPD7525	Registered
0.8111	Intermediate Similarity	NPD7524	Approved
0.7931	Intermediate Similarity	NPD6931	Approved
0.7931	Intermediate Similarity	NPD6930	Phase 2
0.7912	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6933	Approved
0.7865	Intermediate Similarity	NPD6695	Phase 3
0.7816	Intermediate Similarity	NPD6929	Approved
0.7778	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7339	Approved
0.7765	Intermediate Similarity	NPD6942	Approved
0.7727	Intermediate Similarity	NPD7514	Phase 3
0.7647	Intermediate Similarity	NPD6926	Approved
0.7647	Intermediate Similarity	NPD6924	Approved
0.7586	Intermediate Similarity	NPD5776	Phase 2
0.7586	Intermediate Similarity	NPD6925	Approved
0.7558	Intermediate Similarity	NPD8264	Approved
0.7528	Intermediate Similarity	NPD4748	Discontinued
0.7528	Intermediate Similarity	NPD7332	Phase 2
0.7527	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD6893	Approved
0.75	Intermediate Similarity	NPD7145	Approved
0.7471	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6902	Approved
0.7386	Intermediate Similarity	NPD6932	Approved
0.7303	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6898	Phase 1
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7222	Intermediate Similarity	NPD6683	Phase 2
0.7216	Intermediate Similarity	NPD7087	Discontinued
0.7209	Intermediate Similarity	NPD4243	Approved
0.7209	Intermediate Similarity	NPD7150	Approved
0.7209	Intermediate Similarity	NPD7152	Approved
0.7209	Intermediate Similarity	NPD7151	Approved
0.7204	Intermediate Similarity	NPD4786	Approved
0.7188	Intermediate Similarity	NPD5328	Approved
0.7176	Intermediate Similarity	NPD6923	Approved
0.7176	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6922	Approved
0.7143	Intermediate Similarity	NPD7509	Discontinued
0.7129	Intermediate Similarity	NPD7638	Approved
0.7093	Intermediate Similarity	NPD7144	Approved
0.7093	Intermediate Similarity	NPD7143	Approved
0.7053	Intermediate Similarity	NPD3618	Phase 1
0.7053	Intermediate Similarity	NPD5279	Phase 3
0.7045	Intermediate Similarity	NPD4785	Approved
0.7045	Intermediate Similarity	NPD4784	Approved
0.7041	Intermediate Similarity	NPD6079	Approved
0.6989	Remote Similarity	NPD3667	Approved
0.697	Remote Similarity	NPD4202	Approved
0.6923	Remote Similarity	NPD5211	Phase 2
0.6869	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD4755	Approved
0.6827	Remote Similarity	NPD4159	Approved
0.6792	Remote Similarity	NPD5141	Approved
0.6789	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD7503	Approved
0.6778	Remote Similarity	NPD5275	Approved
0.6778	Remote Similarity	NPD4190	Phase 3
0.6765	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5221	Approved
0.6765	Remote Similarity	NPD5222	Approved
0.6762	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD7516	Approved
0.6731	Remote Similarity	NPD5286	Approved
0.6731	Remote Similarity	NPD4700	Approved
0.6731	Remote Similarity	NPD5285	Approved
0.6731	Remote Similarity	NPD4696	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6701	Remote Similarity	NPD5280	Approved
0.6701	Remote Similarity	NPD4694	Approved
0.6699	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6607	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD5225	Approved
0.6604	Remote Similarity	NPD5226	Approved
0.6604	Remote Similarity	NPD5224	Approved
0.6604	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD7136	Phase 2
0.6598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6552	Remote Similarity	NPD8294	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6548	Remote Similarity	NPD368	Approved
0.6545	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4754	Approved
0.6542	Remote Similarity	NPD5175	Approved
0.6542	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD7515	Phase 2
0.6535	Remote Similarity	NPD5284	Approved
0.6535	Remote Similarity	NPD5281	Approved
0.6531	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8379	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8380	Approved
0.6496	Remote Similarity	NPD8296	Approved
0.6496	Remote Similarity	NPD8033	Approved
0.6495	Remote Similarity	NPD3668	Phase 3
0.6476	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6458	Remote Similarity	NPD4221	Approved
0.6458	Remote Similarity	NPD4223	Phase 3
0.6455	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6455	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD5329	Approved
0.6422	Remote Similarity	NPD4768	Approved
0.6422	Remote Similarity	NPD6640	Phase 3
0.6422	Remote Similarity	NPD4767	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6383	Remote Similarity	NPD6114	Approved
0.6383	Remote Similarity	NPD6118	Approved
0.6383	Remote Similarity	NPD6115	Approved
0.6383	Remote Similarity	NPD6697	Approved
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD5690	Phase 2
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6355	Remote Similarity	NPD5344	Discontinued
0.6354	Remote Similarity	NPD4139	Approved
0.6354	Remote Similarity	NPD4692	Approved
0.6346	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD5210	Approved
0.6346	Remote Similarity	NPD5695	Phase 3
0.6339	Remote Similarity	NPD7290	Approved
0.6339	Remote Similarity	NPD6883	Approved
0.6339	Remote Similarity	NPD7102	Approved
0.6333	Remote Similarity	NPD4787	Phase 1
0.6327	Remote Similarity	NPD4197	Approved
0.6321	Remote Similarity	NPD5290	Discontinued
0.6311	Remote Similarity	NPD5133	Approved
0.6306	Remote Similarity	NPD4729	Approved
0.6306	Remote Similarity	NPD4730	Approved
0.6306	Remote Similarity	NPD5128	Approved
0.6306	Remote Similarity	NPD6011	Approved
0.6293	Remote Similarity	NPD6009	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD6617	Approved
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6650	Approved
0.6283	Remote Similarity	NPD6847	Approved
0.6283	Remote Similarity	NPD8130	Phase 1
0.6281	Remote Similarity	NPD7507	Approved
0.6275	Remote Similarity	NPD4096	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6271	Remote Similarity	NPD6054	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.6262	Remote Similarity	NPD6404	Discontinued
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6882	Approved
0.6224	Remote Similarity	NPD4788	Approved
0.6214	Remote Similarity	NPD6411	Approved
0.6214	Remote Similarity	NPD8035	Phase 2
0.6214	Remote Similarity	NPD6050	Approved
0.6214	Remote Similarity	NPD8034	Phase 2
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4688	Approved
0.62	Remote Similarity	NPD4138	Approved
0.62	Remote Similarity	NPD5205	Approved
0.62	Remote Similarity	NPD4689	Approved
0.62	Remote Similarity	NPD4519	Discontinued
0.62	Remote Similarity	NPD4623	Approved
0.62	Remote Similarity	NPD4690	Approved
0.62	Remote Similarity	NPD4693	Phase 3
0.6196	Remote Similarity	NPD4732	Discontinued
0.6195	Remote Similarity	NPD5248	Approved
0.6195	Remote Similarity	NPD5135	Approved
0.6195	Remote Similarity	NPD5249	Phase 3
0.6195	Remote Similarity	NPD5247	Approved
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5250	Approved
0.6195	Remote Similarity	NPD5251	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