NPASS Compound

Structure

NPC105208 OpenBabel07101718202D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.7515 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0387 3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0605 3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3914 4.1270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 1.7321 0.0000 0.0000 C 0 0 1 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 -4.7004 5.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 26 1 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 27 1 0 0 0 0 14 17 1 0 0 0 0 15 3 1 1 0 0 0 15 16 1 0 0 0 0 16 25 1 6 0 0 0 17 28 1 1 0 0 0 18 23 1 0 0 0 0 18 29 1 6 0 0 0 19 24 1 0 0 0 0 19 30 1 6 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 26 1 6 0 0 0 23 32 1 6 0 0 0 24 25 1 6 0 0 0 24 27 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 27 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.35
Volume:	494.064
LogP:	3.093
LogD:	3.535
LogS:	-3.501
# Rotatable Bonds:	5
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	5.125
Fsp3:	1.0
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:	-5.018
MDCK Permeability:	2.3797096218913794e-05
Pgp-inhibitor:	0.212
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.075
20% Bioavailability (F20%):	0.8
30% Bioavailability (F30%):	0.775

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	84.05784606933594%
Volume Distribution (VD):	0.663
Pgp-substrate:	7.657223701477051%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	4.206
Half-life (T1/2):	0.256

ADMET: Toxicity

hERG Blockers:	0.207
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.532
Carcinogencity:	0.037
Eye Corrosion:	0.112
Eye Irritation:	0.036
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC105208

Natural Product ID:	NPC105208
*Common Name:**	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-((2R,5S)-5-Hydroxy-6-Methylheptan-2-Yl)-10,13-Dimethylhexadecahydro-1H-Cyclopenta[A]Phenanthrene-3,4,6,8,15-Pentaol
IUPAC Name:	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,4,6,8,15-pentol
Synonyms:
Standard InCHIKey:	ZYJVXGGOTKOCRF-NDCBDQMYSA-N
Standard InCHI:	InChI=1S/C27H48O6/c1-14(2)17(28)7-6-15(3)16-12-19(30)24-25(16,4)11-9-21-26(5)10-8-18(29)23(32)22(26)20(31)13-27(21,24)33/h14-24,28-33H,6-13H2,1-5H3/t15-,16-,17+,18+,19-,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H]([C@@H]([C@@H]3[C@H](C[C@@]21O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463561
PubChem CID:	44584407
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:0002198] Pentahydroxy 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
NPO33455	nardoa tuberculata	Species	Ophidiasteridae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[8377014]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6256	Organism	Sphaerechinus granularis	Sphaerechinus granularis	LD50	=	1.0	10'-6M	PMID[482621]

☑ 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 NPC105208 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	424
0.1-0.2	4470
0.2-0.3	13681
0.3-0.4	11217
0.4-0.5	5065
0.5-0.6	4403
0.6-0.7	2536
0.7-0.8	714
0.8-0.85	100
0.85-0.9	44
0.9-0.95	23
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192046
1.0	High Similarity	NPC302578
1.0	High Similarity	NPC477227
1.0	High Similarity	NPC128951
0.9861	High Similarity	NPC18857
0.9861	High Similarity	NPC67657
0.9859	High Similarity	NPC163597
0.9722	High Similarity	NPC185915
0.9718	High Similarity	NPC243027
0.9718	High Similarity	NPC196136
0.9718	High Similarity	NPC158208
0.9718	High Similarity	NPC317242
0.9577	High Similarity	NPC228994
0.9577	High Similarity	NPC192501
0.9577	High Similarity	NPC10476
0.9577	High Similarity	NPC304499
0.9459	High Similarity	NPC287452
0.9437	High Similarity	NPC153719
0.9437	High Similarity	NPC470610
0.9324	High Similarity	NPC147993
0.9306	High Similarity	NPC48795
0.9221	High Similarity	NPC478054
0.92	High Similarity	NPC269333
0.9155	High Similarity	NPC251201
0.9155	High Similarity	NPC63588
0.9155	High Similarity	NPC232925
0.9014	High Similarity	NPC470833
0.9014	High Similarity	NPC477820
0.9014	High Similarity	NPC66407
0.9014	High Similarity	NPC107919
0.8987	High Similarity	NPC266651
0.8947	High Similarity	NPC477282
0.8947	High Similarity	NPC81074
0.8875	High Similarity	NPC121981
0.8873	High Similarity	NPC474756
0.8846	High Similarity	NPC202688
0.8846	High Similarity	NPC60018
0.8846	High Similarity	NPC154043
0.8846	High Similarity	NPC475388
0.8831	High Similarity	NPC16449
0.8784	High Similarity	NPC475458
0.8767	High Similarity	NPC127094
0.8767	High Similarity	NPC1340
0.8767	High Similarity	NPC252182
0.8767	High Similarity	NPC470071
0.8767	High Similarity	NPC187471
0.8734	High Similarity	NPC85095
0.8734	High Similarity	NPC216420
0.8734	High Similarity	NPC211135
0.8732	High Similarity	NPC63190
0.8684	High Similarity	NPC474574
0.8684	High Similarity	NPC133596
0.8684	High Similarity	NPC64081
0.8684	High Similarity	NPC476233
0.8684	High Similarity	NPC11907
0.863	High Similarity	NPC231945
0.863	High Similarity	NPC192192
0.8625	High Similarity	NPC255882
0.8625	High Similarity	NPC320824
0.8592	High Similarity	NPC44122
0.8554	High Similarity	NPC109744
0.8553	High Similarity	NPC470145
0.8553	High Similarity	NPC477602
0.8553	High Similarity	NPC473916
0.8553	High Similarity	NPC477601
0.85	High Similarity	NPC232023
0.8493	Intermediate Similarity	NPC254037
0.8493	Intermediate Similarity	NPC129829
0.8493	Intermediate Similarity	NPC470830
0.8493	Intermediate Similarity	NPC241085
0.8493	Intermediate Similarity	NPC299948
0.8452	Intermediate Similarity	NPC475751
0.8452	Intermediate Similarity	NPC473956
0.8451	Intermediate Similarity	NPC472946
0.8451	Intermediate Similarity	NPC190827
0.8451	Intermediate Similarity	NPC243469
0.8451	Intermediate Similarity	NPC475943
0.8434	Intermediate Similarity	NPC128475
0.8421	Intermediate Similarity	NPC131584
0.8421	Intermediate Similarity	NPC270306
0.8421	Intermediate Similarity	NPC139765
0.8421	Intermediate Similarity	NPC91387
0.8421	Intermediate Similarity	NPC231680
0.8415	Intermediate Similarity	NPC471240
0.8356	Intermediate Similarity	NPC472741
0.8353	Intermediate Similarity	NPC293609
0.8333	Intermediate Similarity	NPC471769
0.8333	Intermediate Similarity	NPC471045
0.8313	Intermediate Similarity	NPC474657
0.8313	Intermediate Similarity	NPC186145
0.8313	Intermediate Similarity	NPC5943
0.8313	Intermediate Similarity	NPC161928
0.8313	Intermediate Similarity	NPC210658
0.8313	Intermediate Similarity	NPC263802
0.831	Intermediate Similarity	NPC118937
0.831	Intermediate Similarity	NPC167995
0.831	Intermediate Similarity	NPC281540
0.831	Intermediate Similarity	NPC159654
0.8293	Intermediate Similarity	NPC273290
0.8293	Intermediate Similarity	NPC232044
0.8267	Intermediate Similarity	NPC157422
0.8267	Intermediate Similarity	NPC131506
0.8267	Intermediate Similarity	NPC109457
0.8267	Intermediate Similarity	NPC157777
0.8267	Intermediate Similarity	NPC100586
0.8256	Intermediate Similarity	NPC277774
0.8243	Intermediate Similarity	NPC99264
0.8235	Intermediate Similarity	NPC279329
0.8228	Intermediate Similarity	NPC476176
0.8219	Intermediate Similarity	NPC473230
0.8219	Intermediate Similarity	NPC48079
0.8219	Intermediate Similarity	NPC475884
0.8214	Intermediate Similarity	NPC475664
0.8193	Intermediate Similarity	NPC472272
0.8193	Intermediate Similarity	NPC155531
0.8193	Intermediate Similarity	NPC6605
0.8193	Intermediate Similarity	NPC215968
0.8193	Intermediate Similarity	NPC201273
0.8193	Intermediate Similarity	NPC476726
0.8193	Intermediate Similarity	NPC131365
0.8193	Intermediate Similarity	NPC476727
0.8171	Intermediate Similarity	NPC227260
0.8169	Intermediate Similarity	NPC249078
0.8169	Intermediate Similarity	NPC114891
0.8169	Intermediate Similarity	NPC236099
0.8169	Intermediate Similarity	NPC209686
0.8161	Intermediate Similarity	NPC3538
0.8161	Intermediate Similarity	NPC113500
0.8161	Intermediate Similarity	NPC477224
0.8158	Intermediate Similarity	NPC473238
0.8158	Intermediate Similarity	NPC472341
0.8148	Intermediate Similarity	NPC470611
0.8148	Intermediate Similarity	NPC121121
0.814	Intermediate Similarity	NPC36372
0.8133	Intermediate Similarity	NPC282454
0.8125	Intermediate Similarity	NPC474714
0.8125	Intermediate Similarity	NPC78545
0.8125	Intermediate Similarity	NPC470609
0.8125	Intermediate Similarity	NPC71535
0.8118	Intermediate Similarity	NPC20822
0.8118	Intermediate Similarity	NPC473472
0.8101	Intermediate Similarity	NPC477819
0.8101	Intermediate Similarity	NPC31828
0.8101	Intermediate Similarity	NPC477817
0.8095	Intermediate Similarity	NPC477600
0.8082	Intermediate Similarity	NPC142712
0.8072	Intermediate Similarity	NPC290612
0.8068	Intermediate Similarity	NPC92196
0.8056	Intermediate Similarity	NPC94897
0.8052	Intermediate Similarity	NPC477508
0.8052	Intermediate Similarity	NPC470151
0.8049	Intermediate Similarity	NPC470070
0.8049	Intermediate Similarity	NPC477285
0.8049	Intermediate Similarity	NPC111582
0.8046	Intermediate Similarity	NPC182740
0.8046	Intermediate Similarity	NPC122083
0.8046	Intermediate Similarity	NPC311246
0.8046	Intermediate Similarity	NPC256104
0.8046	Intermediate Similarity	NPC167644
0.8046	Intermediate Similarity	NPC211845
0.8028	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC218585
0.8028	Intermediate Similarity	NPC71460
0.8026	Intermediate Similarity	NPC478103
0.8026	Intermediate Similarity	NPC477823
0.8026	Intermediate Similarity	NPC324984
0.8026	Intermediate Similarity	NPC323900
0.8026	Intermediate Similarity	NPC477822
0.8026	Intermediate Similarity	NPC473552
0.8026	Intermediate Similarity	NPC477821
0.8025	Intermediate Similarity	NPC469745
0.8023	Intermediate Similarity	NPC223143
0.8	Intermediate Similarity	NPC281004
0.8	Intermediate Similarity	NPC473436
0.7978	Intermediate Similarity	NPC473287
0.7976	Intermediate Similarity	NPC477283
0.7975	Intermediate Similarity	NPC171658
0.7955	Intermediate Similarity	NPC309866
0.7955	Intermediate Similarity	NPC473503
0.7952	Intermediate Similarity	NPC256567
0.7952	Intermediate Similarity	NPC50438
0.7949	Intermediate Similarity	NPC472950
0.7949	Intermediate Similarity	NPC472952
0.7945	Intermediate Similarity	NPC473276
0.7945	Intermediate Similarity	NPC474380
0.7945	Intermediate Similarity	NPC260116
0.7945	Intermediate Similarity	NPC41577
0.7931	Intermediate Similarity	NPC5632
0.7931	Intermediate Similarity	NPC204881
0.7931	Intermediate Similarity	NPC473066
0.7931	Intermediate Similarity	NPC149966
0.7931	Intermediate Similarity	NPC219516
0.7931	Intermediate Similarity	NPC473830
0.7927	Intermediate Similarity	NPC296734
0.7927	Intermediate Similarity	NPC477286
0.7927	Intermediate Similarity	NPC317066
0.7927	Intermediate Similarity	NPC286719
0.7907	Intermediate Similarity	NPC228059
0.7907	Intermediate Similarity	NPC105495
0.7907	Intermediate Similarity	NPC102725

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 NPC105208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	4444
0.2-0.3	2965
0.3-0.4	731
0.4-0.5	268
0.5-0.6	194
0.6-0.7	99
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9014	High Similarity	NPD4267	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4787	Phase 1
0.7683	Intermediate Similarity	NPD6928	Phase 2
0.7654	Intermediate Similarity	NPD6118	Approved
0.7654	Intermediate Similarity	NPD6114	Approved
0.7654	Intermediate Similarity	NPD6115	Approved
0.7654	Intermediate Similarity	NPD6697	Approved
0.7531	Intermediate Similarity	NPD6116	Phase 1
0.747	Intermediate Similarity	NPD7525	Registered
0.7444	Intermediate Similarity	NPD8171	Discontinued
0.7407	Intermediate Similarity	NPD6117	Approved
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD371	Approved
0.7284	Intermediate Similarity	NPD3703	Phase 2
0.7215	Intermediate Similarity	NPD4245	Approved
0.7215	Intermediate Similarity	NPD4244	Approved
0.716	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3698	Phase 2
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5360	Phase 3
0.6962	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4789	Approved
0.6703	Remote Similarity	NPD7524	Approved
0.67	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6700	Approved
0.6667	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4748	Discontinued
0.6596	Remote Similarity	NPD6703	Approved
0.6596	Remote Similarity	NPD6702	Approved
0.6588	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7991	Discontinued
0.6556	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7516	Approved
0.6506	Remote Similarity	NPD4758	Discontinued
0.6484	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6930	Phase 2
0.6477	Remote Similarity	NPD6931	Approved
0.6471	Remote Similarity	NPD3702	Approved
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6444	Remote Similarity	NPD6695	Phase 3
0.6444	Remote Similarity	NPD4788	Approved
0.6437	Remote Similarity	NPD3671	Phase 1
0.6437	Remote Similarity	NPD5364	Discontinued
0.6429	Remote Similarity	NPD4755	Approved
0.6422	Remote Similarity	NPD7327	Approved
0.6422	Remote Similarity	NPD7328	Approved
0.64	Remote Similarity	NPD4159	Approved
0.6395	Remote Similarity	NPD6933	Approved
0.6386	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD6929	Approved
0.6354	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.6322	Remote Similarity	NPD6932	Approved
0.631	Remote Similarity	NPD4243	Approved
0.631	Remote Similarity	NPD5777	Approved
0.631	Remote Similarity	NPD6081	Approved
0.63	Remote Similarity	NPD5285	Approved
0.63	Remote Similarity	NPD4700	Approved
0.63	Remote Similarity	NPD4696	Approved
0.63	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD8379	Approved
0.6238	Remote Similarity	NPD1700	Approved
0.62	Remote Similarity	NPD7638	Approved
0.618	Remote Similarity	NPD6683	Phase 2
0.6176	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD5225	Approved
0.6176	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD5226	Approved
0.617	Remote Similarity	NPD7750	Discontinued
0.6163	Remote Similarity	NPD1810	Approved
0.6163	Remote Similarity	NPD4785	Approved
0.6163	Remote Similarity	NPD6926	Approved
0.6163	Remote Similarity	NPD4784	Approved
0.6163	Remote Similarity	NPD1811	Approved
0.6163	Remote Similarity	NPD6924	Approved
0.6161	Remote Similarity	NPD8294	Approved
0.6161	Remote Similarity	NPD8377	Approved
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6139	Remote Similarity	NPD7640	Approved
0.6139	Remote Similarity	NPD8418	Phase 2
0.6139	Remote Similarity	NPD7639	Approved
0.6136	Remote Similarity	NPD6925	Approved
0.6136	Remote Similarity	NPD5776	Phase 2
0.6129	Remote Similarity	NPD6893	Approved
0.6117	Remote Similarity	NPD5174	Approved
0.6117	Remote Similarity	NPD5175	Approved
0.6111	Remote Similarity	NPD7514	Phase 3
0.6106	Remote Similarity	NPD8033	Approved
0.6098	Remote Similarity	NPD4224	Phase 2
0.6078	Remote Similarity	NPD5223	Approved
0.6067	Remote Similarity	NPD7145	Approved
0.6064	Remote Similarity	NPD8308	Discontinued
0.6058	Remote Similarity	NPD5141	Approved
0.6056	Remote Similarity	NPD384	Approved
0.6056	Remote Similarity	NPD385	Approved
0.6055	Remote Similarity	NPD4632	Approved
0.6055	Remote Similarity	NPD8133	Approved
0.6042	Remote Similarity	NPD4753	Phase 2
0.6042	Remote Similarity	NPD5328	Approved
0.6038	Remote Similarity	NPD7320	Approved
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6022	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD4767	Approved
0.5981	Remote Similarity	NPD6372	Approved
0.5981	Remote Similarity	NPD6373	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD8297	Approved
0.5962	Remote Similarity	NPD4754	Approved
0.5943	Remote Similarity	NPD5701	Approved
0.5943	Remote Similarity	NPD6412	Phase 2
0.5943	Remote Similarity	NPD5697	Approved
0.5941	Remote Similarity	NPD7920	Phase 3
0.5941	Remote Similarity	NPD7919	Phase 3
0.5934	Remote Similarity	NPD7509	Discontinued
0.5934	Remote Similarity	NPD7332	Phase 2
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5918	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD7087	Discontinued
0.5915	Remote Similarity	NPD386	Approved
0.5915	Remote Similarity	NPD388	Approved
0.5909	Remote Similarity	NPD4190	Phase 3
0.5909	Remote Similarity	NPD5275	Approved
0.5897	Remote Similarity	NPD7507	Approved
0.5895	Remote Similarity	NPD3618	Phase 1
0.5888	Remote Similarity	NPD4730	Approved
0.5888	Remote Similarity	NPD4729	Approved
0.5888	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD7319	Approved
0.5882	Remote Similarity	NPD8088	Phase 1
0.5877	Remote Similarity	NPD6319	Approved
0.5877	Remote Similarity	NPD6059	Approved
0.5877	Remote Similarity	NPD6054	Approved
0.5872	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD6649	Approved
0.5872	Remote Similarity	NPD6617	Approved
0.587	Remote Similarity	NPD6898	Phase 1
0.587	Remote Similarity	NPD6902	Approved
0.5851	Remote Similarity	NPD3665	Phase 1
0.5851	Remote Similarity	NPD3666	Approved
0.5851	Remote Similarity	NPD3133	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5826	Remote Similarity	NPD7503	Approved
0.5824	Remote Similarity	NPD4195	Approved
0.5818	Remote Similarity	NPD6882	Approved
0.5814	Remote Similarity	NPD2687	Approved
0.5814	Remote Similarity	NPD2254	Approved
0.5814	Remote Similarity	NPD2686	Approved
0.5806	Remote Similarity	NPD3667	Approved
0.5804	Remote Similarity	NPD6940	Discontinued
0.5784	Remote Similarity	NPD6083	Phase 2
0.5784	Remote Similarity	NPD6084	Phase 2
0.578	Remote Similarity	NPD5250	Approved
0.578	Remote Similarity	NPD5249	Phase 3
0.578	Remote Similarity	NPD5247	Approved
0.578	Remote Similarity	NPD5248	Approved
0.578	Remote Similarity	NPD5251	Approved
0.5776	Remote Similarity	NPD6370	Approved
0.5752	Remote Similarity	NPD6009	Approved
0.5747	Remote Similarity	NPD7151	Approved
0.5747	Remote Similarity	NPD7150	Approved
0.5747	Remote Similarity	NPD7152	Approved
0.5743	Remote Similarity	NPD5210	Approved
0.5743	Remote Similarity	NPD4629	Approved
0.5741	Remote Similarity	NPD6011	Approved
0.5741	Remote Similarity	NPD8174	Phase 2
0.5727	Remote Similarity	NPD5217	Approved
0.5727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5216	Approved
0.5727	Remote Similarity	NPD5215	Approved
0.57	Remote Similarity	NPD6399	Phase 3
0.5698	Remote Similarity	NPD6923	Approved
0.5698	Remote Similarity	NPD6922	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