NPASS Compound

Structure

NPC48795 OpenBabel07101718302D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.2142 -5.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5669 -6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9271 -4.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2812 1.1910 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 2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 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 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2435 -3.1928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 17 3 1 1 0 0 0 17 24 1 0 0 0 0 18 7 1 1 0 0 0 19 31 1 1 0 0 0 20 15 1 6 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 23 32 1 6 0 0 0 24 26 1 0 0 0 0 24 29 1 1 0 0 0 25 27 1 0 0 0 0 25 29 1 1 0 0 0 26 27 1 0 0 0 0 26 33 1 1 0 0 0 27 34 1 1 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.38
Volume:	519.865
LogP:	4.645
LogD:	4.782
LogS:	-3.905
# Rotatable Bonds:	7
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	5.066
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:	-4.909
MDCK Permeability:	5.876836075913161e-05
Pgp-inhibitor:	0.905
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.854
30% Bioavailability (F30%):	0.459

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	95.54761505126953%
Volume Distribution (VD):	0.816
Pgp-substrate:	1.7987351417541504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.154
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	8.026
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.467
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.952
Carcinogencity:	0.037
Eye Corrosion:	0.986
Eye Irritation:	0.472
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC48795

Natural Product ID:	NPC48795
*Common Name:**	Certonardosterol N1
IUPAC Name:	(3S,5S,6S,8R,9S,10R,13R,14S,15S,16R,17R)-17-[(2R,5R)-5-(2-hydroxyethyl)-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,15,16-tetrol
Synonyms:	Certonardosterol N1
Standard InCHIKey:	CQDRJWAYTUMGAI-OJGOSNDTSA-N
Standard InCHI:	InChI=1S/C29H52O5/c1-16(2)18(10-13-30)7-6-17(3)24-26(33)27(34)25-20-15-23(32)22-14-19(31)8-11-28(22,4)21(20)9-12-29(24,25)5/h16-27,30-34H,6-15H2,1-5H3/t17-,18-,19+,20-,21+,22-,23+,24+,25-,26-,27+,28-,29-/m1/s1
SMILES:	OCC[C@H](C(C)C)CC[C@H]([C@H]1[C@@H](O)[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463280
PubChem CID:	11431595
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.82	ug ml-1	PMID[475080]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	0.9	ug ml-1	PMID[475080]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[475080]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.43	ug ml-1	PMID[475080]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	1.25	ug ml-1	PMID[475080]

☑ 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 NPC48795 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	402
0.1-0.2	4454
0.2-0.3	15385
0.3-0.4	9947
0.4-0.5	4822
0.5-0.6	4480
0.6-0.7	2374
0.7-0.8	640
0.8-0.85	115
0.85-0.9	43
0.9-0.95	24
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC470610
0.9577	High Similarity	NPC185915
0.9571	High Similarity	NPC317242
0.9565	High Similarity	NPC153719
0.9559	High Similarity	NPC232925
0.9559	High Similarity	NPC251201
0.9559	High Similarity	NPC63588
0.9444	High Similarity	NPC67657
0.9444	High Similarity	NPC18857
0.9437	High Similarity	NPC163597
0.9412	High Similarity	NPC477820
0.9315	High Similarity	NPC287452
0.9306	High Similarity	NPC105208
0.9306	High Similarity	NPC128951
0.9306	High Similarity	NPC302578
0.9306	High Similarity	NPC192046
0.9306	High Similarity	NPC477227
0.9155	High Similarity	NPC304499
0.913	High Similarity	NPC66407
0.9028	High Similarity	NPC196136
0.9028	High Similarity	NPC243027
0.9028	High Similarity	NPC158208
0.8971	High Similarity	NPC44122
0.8889	High Similarity	NPC10476
0.8889	High Similarity	NPC192501
0.8889	High Similarity	NPC228994
0.8873	High Similarity	NPC1340
0.8873	High Similarity	NPC187471
0.8873	High Similarity	NPC252182
0.8873	High Similarity	NPC127094
0.8873	High Similarity	NPC470071
0.8857	High Similarity	NPC107919
0.8841	High Similarity	NPC63190
0.8831	High Similarity	NPC478054
0.8784	High Similarity	NPC64081
0.8784	High Similarity	NPC474574
0.8732	High Similarity	NPC192192
0.8701	High Similarity	NPC475388
0.8676	High Similarity	NPC281540
0.8676	High Similarity	NPC118937
0.8676	High Similarity	NPC159654
0.8676	High Similarity	NPC167995
0.8667	High Similarity	NPC147993
0.8649	High Similarity	NPC477601
0.8649	High Similarity	NPC473916
0.8649	High Similarity	NPC477602
0.8592	High Similarity	NPC241085
0.8592	High Similarity	NPC129829
0.8592	High Similarity	NPC470830
0.8592	High Similarity	NPC254037
0.8592	High Similarity	NPC299948
0.8592	High Similarity	NPC470833
0.8553	High Similarity	NPC81074
0.8553	High Similarity	NPC477282
0.8553	High Similarity	NPC269333
0.8551	High Similarity	NPC243469
0.8551	High Similarity	NPC190827
0.8551	High Similarity	NPC475943
0.8533	High Similarity	NPC476233
0.8533	High Similarity	NPC11907
0.8533	High Similarity	NPC133596
0.8529	High Similarity	NPC236099
0.8529	High Similarity	NPC209686
0.8529	High Similarity	NPC249078
0.8529	High Similarity	NPC114891
0.8514	High Similarity	NPC91387
0.8514	High Similarity	NPC270306
0.8514	High Similarity	NPC231680
0.8481	Intermediate Similarity	NPC255882
0.8472	Intermediate Similarity	NPC231945
0.8462	Intermediate Similarity	NPC470611
0.8451	Intermediate Similarity	NPC474756
0.8451	Intermediate Similarity	NPC472741
0.8442	Intermediate Similarity	NPC71535
0.8442	Intermediate Similarity	NPC470609
0.8442	Intermediate Similarity	NPC78545
0.8429	Intermediate Similarity	NPC142712
0.8421	Intermediate Similarity	NPC471045
0.8421	Intermediate Similarity	NPC477819
0.8421	Intermediate Similarity	NPC477817
0.84	Intermediate Similarity	NPC470145
0.8382	Intermediate Similarity	NPC148174
0.8382	Intermediate Similarity	NPC218585
0.8382	Intermediate Similarity	NPC71460
0.8378	Intermediate Similarity	NPC475458
0.8375	Intermediate Similarity	NPC266651
0.8375	Intermediate Similarity	NPC273290
0.8375	Intermediate Similarity	NPC232044
0.8356	Intermediate Similarity	NPC131506
0.8356	Intermediate Similarity	NPC157777
0.8356	Intermediate Similarity	NPC109457
0.8356	Intermediate Similarity	NPC478103
0.8356	Intermediate Similarity	NPC157422
0.8356	Intermediate Similarity	NPC100586
0.8333	Intermediate Similarity	NPC99264
0.8333	Intermediate Similarity	NPC469745
0.8312	Intermediate Similarity	NPC476176
0.831	Intermediate Similarity	NPC473230
0.831	Intermediate Similarity	NPC475884
0.831	Intermediate Similarity	NPC48079
0.8286	Intermediate Similarity	NPC474380
0.8286	Intermediate Similarity	NPC41577
0.8286	Intermediate Similarity	NPC473276
0.8286	Intermediate Similarity	NPC472946
0.8272	Intermediate Similarity	NPC476727
0.8272	Intermediate Similarity	NPC476726
0.8272	Intermediate Similarity	NPC121981
0.8272	Intermediate Similarity	NPC471240
0.8272	Intermediate Similarity	NPC472272
0.8267	Intermediate Similarity	NPC139765
0.8267	Intermediate Similarity	NPC131584
0.825	Intermediate Similarity	NPC227260
0.8243	Intermediate Similarity	NPC472341
0.8243	Intermediate Similarity	NPC473238
0.8228	Intermediate Similarity	NPC60018
0.8228	Intermediate Similarity	NPC296734
0.8228	Intermediate Similarity	NPC121121
0.8228	Intermediate Similarity	NPC154043
0.8228	Intermediate Similarity	NPC202688
0.8219	Intermediate Similarity	NPC282454
0.8205	Intermediate Similarity	NPC16449
0.8193	Intermediate Similarity	NPC102725
0.8171	Intermediate Similarity	NPC210658
0.8171	Intermediate Similarity	NPC474657
0.8171	Intermediate Similarity	NPC186145
0.8171	Intermediate Similarity	NPC161928
0.8143	Intermediate Similarity	NPC69149
0.8133	Intermediate Similarity	NPC477508
0.8125	Intermediate Similarity	NPC193870
0.8125	Intermediate Similarity	NPC477285
0.8125	Intermediate Similarity	NPC470070
0.8125	Intermediate Similarity	NPC85095
0.8125	Intermediate Similarity	NPC111582
0.8125	Intermediate Similarity	NPC141941
0.8125	Intermediate Similarity	NPC216420
0.8125	Intermediate Similarity	NPC211135
0.8125	Intermediate Similarity	NPC110778
0.8125	Intermediate Similarity	NPC232023
0.8108	Intermediate Similarity	NPC323900
0.8108	Intermediate Similarity	NPC477823
0.8108	Intermediate Similarity	NPC477821
0.8108	Intermediate Similarity	NPC324984
0.8108	Intermediate Similarity	NPC473552
0.8108	Intermediate Similarity	NPC477822
0.8095	Intermediate Similarity	NPC223143
0.8077	Intermediate Similarity	NPC24504
0.8072	Intermediate Similarity	NPC281004
0.8072	Intermediate Similarity	NPC475664
0.8072	Intermediate Similarity	NPC128475
0.8052	Intermediate Similarity	NPC171658
0.8028	Intermediate Similarity	NPC260116
0.8025	Intermediate Similarity	NPC475798
0.8025	Intermediate Similarity	NPC320824
0.8025	Intermediate Similarity	NPC127606
0.8	Intermediate Similarity	NPC286719
0.8	Intermediate Similarity	NPC473066
0.8	Intermediate Similarity	NPC36372
0.8	Intermediate Similarity	NPC477286
0.7976	Intermediate Similarity	NPC105495
0.7976	Intermediate Similarity	NPC20822
0.7976	Intermediate Similarity	NPC473472
0.7976	Intermediate Similarity	NPC109744
0.7976	Intermediate Similarity	NPC228059
0.7975	Intermediate Similarity	NPC248944
0.7975	Intermediate Similarity	NPC47149
0.7975	Intermediate Similarity	NPC7479
0.7975	Intermediate Similarity	NPC257296
0.7949	Intermediate Similarity	NPC34046
0.7949	Intermediate Similarity	NPC475
0.7949	Intermediate Similarity	NPC472502
0.7949	Intermediate Similarity	NPC471769
0.7949	Intermediate Similarity	NPC80089
0.7949	Intermediate Similarity	NPC224802
0.7949	Intermediate Similarity	NPC324700
0.7949	Intermediate Similarity	NPC472499
0.7949	Intermediate Similarity	NPC171426
0.7949	Intermediate Similarity	NPC472500
0.7941	Intermediate Similarity	NPC476735
0.7927	Intermediate Similarity	NPC290612
0.7922	Intermediate Similarity	NPC91573
0.7907	Intermediate Similarity	NPC277774
0.7901	Intermediate Similarity	NPC477818
0.7895	Intermediate Similarity	NPC478130
0.7895	Intermediate Similarity	NPC472503
0.7895	Intermediate Similarity	NPC308440
0.7882	Intermediate Similarity	NPC65550
0.7882	Intermediate Similarity	NPC473956
0.7882	Intermediate Similarity	NPC475751
0.7882	Intermediate Similarity	NPC473542
0.7882	Intermediate Similarity	NPC279329
0.7875	Intermediate Similarity	NPC190940
0.7875	Intermediate Similarity	NPC73515
0.7867	Intermediate Similarity	NPC195530
0.7867	Intermediate Similarity	NPC473279
0.7867	Intermediate Similarity	NPC127283
0.7867	Intermediate Similarity	NPC8004
0.7848	Intermediate Similarity	NPC201276
0.7848	Intermediate Similarity	NPC476316
0.7848	Intermediate Similarity	NPC220379
0.7848	Intermediate Similarity	NPC80891

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 NPC48795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	4419
0.2-0.3	3046
0.3-0.4	710
0.4-0.5	253
0.5-0.6	213
0.6-0.7	78
0.7-0.8	20
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD4267	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD4787	Phase 1
0.7975	Intermediate Similarity	NPD6928	Phase 2
0.7949	Intermediate Similarity	NPD6115	Approved
0.7949	Intermediate Similarity	NPD6118	Approved
0.7949	Intermediate Similarity	NPD6114	Approved
0.7949	Intermediate Similarity	NPD6697	Approved
0.7821	Intermediate Similarity	NPD6116	Phase 1
0.7692	Intermediate Similarity	NPD6117	Approved
0.7632	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3703	Phase 2
0.7531	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD4244	Approved
0.75	Intermediate Similarity	NPD8171	Discontinued
0.75	Intermediate Similarity	NPD4245	Approved
0.7436	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3698	Phase 2
0.7368	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4789	Approved
0.7013	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5360	Phase 3
0.6889	Remote Similarity	NPD6700	Approved
0.6889	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6703	Approved
0.6813	Remote Similarity	NPD6702	Approved
0.6774	Remote Similarity	NPD7991	Discontinued
0.6735	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD371	Approved
0.6707	Remote Similarity	NPD7339	Approved
0.6707	Remote Similarity	NPD6942	Approved
0.6706	Remote Similarity	NPD4748	Discontinued
0.6705	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3671	Phase 1
0.6582	Remote Similarity	NPD6705	Phase 1
0.6556	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4758	Discontinued
0.6543	Remote Similarity	NPD6081	Approved
0.6543	Remote Similarity	NPD5777	Approved
0.6506	Remote Similarity	NPD3702	Approved
0.6477	Remote Similarity	NPD4788	Approved
0.6471	Remote Similarity	NPD5364	Discontinued
0.6452	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD8034	Phase 2
0.6429	Remote Similarity	NPD6933	Approved
0.6408	Remote Similarity	NPD4634	Approved
0.6395	Remote Similarity	NPD7645	Phase 2
0.6392	Remote Similarity	NPD7638	Approved
0.6383	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD4243	Approved
0.6329	Remote Similarity	NPD4224	Phase 2
0.6327	Remote Similarity	NPD7640	Approved
0.6327	Remote Similarity	NPD7639	Approved
0.6327	Remote Similarity	NPD8418	Phase 2
0.6324	Remote Similarity	NPD384	Approved
0.6324	Remote Similarity	NPD385	Approved
0.6289	Remote Similarity	NPD4755	Approved
0.6264	Remote Similarity	NPD8308	Discontinued
0.6237	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4786	Approved
0.6207	Remote Similarity	NPD6929	Approved
0.62	Remote Similarity	NPD7632	Discontinued
0.6196	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD1810	Approved
0.619	Remote Similarity	NPD6924	Approved
0.619	Remote Similarity	NPD4785	Approved
0.619	Remote Similarity	NPD1811	Approved
0.619	Remote Similarity	NPD4784	Approved
0.619	Remote Similarity	NPD6926	Approved
0.6162	Remote Similarity	NPD5285	Approved
0.6162	Remote Similarity	NPD4700	Approved
0.6162	Remote Similarity	NPD5286	Approved
0.6162	Remote Similarity	NPD4696	Approved
0.6147	Remote Similarity	NPD7328	Approved
0.6147	Remote Similarity	NPD7327	Approved
0.6136	Remote Similarity	NPD6931	Approved
0.6136	Remote Similarity	NPD6930	Phase 2
0.6122	Remote Similarity	NPD7919	Phase 3
0.6122	Remote Similarity	NPD7920	Phase 3
0.6111	Remote Similarity	NPD6695	Phase 3
0.6105	Remote Similarity	NPD6079	Approved
0.61	Remote Similarity	NPD5223	Approved
0.6091	Remote Similarity	NPD7516	Approved
0.6087	Remote Similarity	NPD3618	Phase 1
0.6075	Remote Similarity	NPD4632	Approved
0.6061	Remote Similarity	NPD8088	Phase 1
0.6044	Remote Similarity	NPD3665	Phase 1
0.6044	Remote Similarity	NPD3133	Approved
0.6044	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD5224	Approved
0.604	Remote Similarity	NPD5225	Approved
0.604	Remote Similarity	NPD5226	Approved
0.604	Remote Similarity	NPD4633	Approved
0.604	Remote Similarity	NPD5211	Phase 2
0.6036	Remote Similarity	NPD8377	Approved
0.6036	Remote Similarity	NPD8294	Approved
0.6024	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD3667	Approved
0.5982	Remote Similarity	NPD8296	Approved
0.5982	Remote Similarity	NPD8380	Approved
0.5982	Remote Similarity	NPD8378	Approved
0.5982	Remote Similarity	NPD8379	Approved
0.5982	Remote Similarity	NPD8033	Approved
0.5982	Remote Similarity	NPD8335	Approved
0.598	Remote Similarity	NPD4754	Approved
0.598	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD5175	Approved
0.5977	Remote Similarity	NPD5776	Phase 2
0.5977	Remote Similarity	NPD6925	Approved
0.5977	Remote Similarity	NPD6932	Approved
0.5962	Remote Similarity	NPD6412	Phase 2
0.5955	Remote Similarity	NPD7509	Discontinued
0.5952	Remote Similarity	NPD7150	Approved
0.5952	Remote Similarity	NPD7152	Approved
0.5952	Remote Similarity	NPD7151	Approved
0.5942	Remote Similarity	NPD388	Approved
0.5942	Remote Similarity	NPD386	Approved
0.5941	Remote Similarity	NPD4159	Approved
0.593	Remote Similarity	NPD4190	Phase 3
0.593	Remote Similarity	NPD5275	Approved
0.5926	Remote Similarity	NPD8133	Approved
0.5922	Remote Similarity	NPD5141	Approved
0.5909	Remote Similarity	NPD7145	Approved
0.5905	Remote Similarity	NPD6881	Approved
0.5905	Remote Similarity	NPD6899	Approved
0.5905	Remote Similarity	NPD7320	Approved
0.5904	Remote Similarity	NPD6923	Approved
0.5904	Remote Similarity	NPD6922	Approved
0.5895	Remote Similarity	NPD4753	Phase 2
0.5893	Remote Similarity	NPD6319	Approved
0.5893	Remote Similarity	NPD6059	Approved
0.5893	Remote Similarity	NPD6054	Approved
0.5876	Remote Similarity	NPD6399	Phase 3
0.5865	Remote Similarity	NPD4767	Approved
0.5865	Remote Similarity	NPD4768	Approved
0.5859	Remote Similarity	NPD5221	Approved
0.5859	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4697	Phase 3
0.5859	Remote Similarity	NPD5222	Approved
0.5851	Remote Similarity	NPD7750	Discontinued
0.5849	Remote Similarity	NPD6372	Approved
0.5849	Remote Similarity	NPD6373	Approved
0.5843	Remote Similarity	NPD4195	Approved
0.5843	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD7144	Approved
0.5833	Remote Similarity	NPD2687	Approved
0.5833	Remote Similarity	NPD2686	Approved
0.5833	Remote Similarity	NPD2254	Approved
0.5833	Remote Similarity	NPD7143	Approved
0.5818	Remote Similarity	NPD6940	Discontinued
0.581	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD5697	Approved
0.5806	Remote Similarity	NPD6893	Approved
0.58	Remote Similarity	NPD5173	Approved
0.5794	Remote Similarity	NPD6883	Approved
0.5794	Remote Similarity	NPD7290	Approved
0.5794	Remote Similarity	NPD7102	Approved
0.5789	Remote Similarity	NPD6370	Approved
0.5784	Remote Similarity	NPD1700	Approved
0.5778	Remote Similarity	NPD7514	Phase 3
0.5776	Remote Similarity	NPD7507	Approved
0.5773	Remote Similarity	NPD7515	Phase 2
0.5769	Remote Similarity	NPD3198	Approved
0.5766	Remote Similarity	NPD6009	Approved
0.5755	Remote Similarity	NPD5128	Approved
0.5755	Remote Similarity	NPD4730	Approved
0.5755	Remote Similarity	NPD8174	Phase 2
0.5755	Remote Similarity	NPD4729	Approved
0.5755	Remote Similarity	NPD6011	Approved
0.5741	Remote Similarity	NPD6617	Approved
0.5741	Remote Similarity	NPD8130	Phase 1
0.5741	Remote Similarity	NPD6650	Approved
0.5741	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6869	Approved
0.5741	Remote Similarity	NPD6649	Approved
0.5741	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD6902	Approved
0.5702	Remote Similarity	NPD6016	Approved
0.5702	Remote Similarity	NPD6015	Approved
0.5702	Remote Similarity	NPD7503	Approved
0.5701	Remote Similarity	NPD6013	Approved
0.5701	Remote Similarity	NPD6012	Approved
0.5701	Remote Similarity	NPD6014	Approved
0.569	Remote Similarity	NPD7492	Approved
0.5688	Remote Similarity	NPD6882	Approved
0.5678	Remote Similarity	NPD7736	Approved
0.566	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4221	Approved
0.5652	Remote Similarity	NPD4223	Phase 3
0.5652	Remote Similarity	NPD5988	Approved
0.5648	Remote Similarity	NPD5250	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