NPASS Compound

Structure

NPC31828 OpenBabel07101718332D 32 35 0 0 1 0 0 0 0 0999 V2000 4.3914 -4.1270 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 5.4207 -1.6896 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 -2.5981 2.5000 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 0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7734 -2.2248 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 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 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 -3.4641 -0.0000 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 1.0000 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 5.0605 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7515 -2.4328 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 -2.5981 1.5000 0.0000 C 0 0 1 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 -1.7321 1.0000 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 -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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 0.0000 0.0000 0.0000 C 0 0 1 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 -1.7321 -2.0000 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 24 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 21 1 0 0 0 0 20 5 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 6 0 0 0 23 30 1 6 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 26 27 1 6 0 0 0 26 29 1 0 0 0 0 27 6 1 6 0 0 0 28 7 1 6 0 0 0 29 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.38
Volume:	499.648
LogP:	5.685
LogD:	5.303
LogS:	-5.178
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	5.026
Fsp3:	0.931
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.728
MDCK Permeability:	2.0432558812899515e-05
Pgp-inhibitor:	0.75
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.156

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.254
Plasma Protein Binding (PPB):	95.44780731201172%
Volume Distribution (VD):	0.904
Pgp-substrate:	2.178525447845459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.515
CYP3A4-inhibitor:	0.539
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	8.569
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.64
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.462
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.826
Carcinogencity:	0.087
Eye Corrosion:	0.75
Eye Irritation:	0.132
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC31828

Natural Product ID:	NPC31828
*Common Name:**	(3S,4S,5S,8R,9S,10S,11S,13R,14R,17R)-4,10,13-Trimethyl-17-((R)-6-Methyl-5-Methyleneheptan-2-Yl)Hexadecahydro-1H-Cyclopenta[A]Phenanthrene-3,8,11-Triol
IUPAC Name:	(3S,4S,5S,8R,9S,10S,11S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,8,11-triol
Synonyms:
Standard InCHIKey:	VFYHLCIHPSUCBD-RLMSMOSBSA-N
Standard InCHI:	InChI=1S/C29H50O3/c1-17(2)18(3)8-9-19(4)21-10-11-25-28(21,7)16-24(31)26-27(6)14-13-23(30)20(5)22(27)12-15-29(25,26)32/h17,19-26,30-32H,3,8-16H2,1-2,4-7H3/t19-,20+,21-,22+,23+,24+,25-,26-,27+,28-,29-/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)C[C@@H]([C@@H]1[C@@]3(C)CC[C@@H]([C@@H](C)[C@@H]3CC[C@@]21O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2322190
PubChem CID:	42604058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO17094	Sinularia depressa	Species	Alcyoniidae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Activity	=	20.1	%	PMID[509995]

☑ 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 NPC31828 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	177
0.1-0.2	2171
0.2-0.3	8675
0.3-0.4	15467
0.4-0.5	5926
0.5-0.6	4793
0.6-0.7	3911
0.7-0.8	1283
0.8-0.85	172
0.85-0.9	82
0.9-0.95	39
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC472742
0.9595	High Similarity	NPC475727
0.9595	High Similarity	NPC116119
0.9595	High Similarity	NPC80297
0.9467	High Similarity	NPC475679
0.9444	High Similarity	NPC472503
0.9444	High Similarity	NPC308440
0.9351	High Similarity	NPC470929
0.9351	High Similarity	NPC216420
0.9351	High Similarity	NPC232023
0.9351	High Similarity	NPC85095
0.9351	High Similarity	NPC211135
0.9324	High Similarity	NPC202540
0.9315	High Similarity	NPC3403
0.9231	High Similarity	NPC86238
0.92	High Similarity	NPC477819
0.92	High Similarity	NPC477817
0.9189	High Similarity	NPC93662
0.9189	High Similarity	NPC278091
0.9189	High Similarity	NPC78067
0.9189	High Similarity	NPC91573
0.9167	High Similarity	NPC111234
0.9103	High Similarity	NPC113978
0.9079	High Similarity	NPC476316
0.9054	High Similarity	NPC70982
0.9054	High Similarity	NPC104387
0.9054	High Similarity	NPC240235
0.9054	High Similarity	NPC185536
0.9054	High Similarity	NPC230704
0.9054	High Similarity	NPC231256
0.9054	High Similarity	NPC178383
0.9054	High Similarity	NPC103822
0.9054	High Similarity	NPC212879
0.9028	High Similarity	NPC45296
0.9	High Similarity	NPC201273
0.9	High Similarity	NPC121981
0.8961	High Similarity	NPC71535
0.8961	High Similarity	NPC78545
0.8947	High Similarity	NPC42853
0.8947	High Similarity	NPC472342
0.8947	High Similarity	NPC472501
0.8947	High Similarity	NPC301707
0.8947	High Similarity	NPC285761
0.8947	High Similarity	NPC472499
0.8947	High Similarity	NPC472500
0.8933	High Similarity	NPC86305
0.8933	High Similarity	NPC14112
0.8919	High Similarity	NPC145552
0.8919	High Similarity	NPC5046
0.8919	High Similarity	NPC196358
0.8919	High Similarity	NPC192638
0.8919	High Similarity	NPC49168
0.8919	High Similarity	NPC254509
0.8919	High Similarity	NPC62657
0.8919	High Similarity	NPC25511
0.8889	High Similarity	NPC477600
0.8846	High Similarity	NPC470383
0.8831	High Similarity	NPC80530
0.8831	High Similarity	NPC24504
0.8831	High Similarity	NPC49599
0.8831	High Similarity	NPC49627
0.8831	High Similarity	NPC273410
0.8816	High Similarity	NPC260301
0.8816	High Similarity	NPC212241
0.8816	High Similarity	NPC257191
0.8816	High Similarity	NPC248830
0.8816	High Similarity	NPC119355
0.8816	High Similarity	NPC307336
0.8816	High Similarity	NPC331618
0.88	High Similarity	NPC200243
0.8784	High Similarity	NPC195489
0.878	High Similarity	NPC473436
0.8765	High Similarity	NPC269058
0.8765	High Similarity	NPC6605
0.8765	High Similarity	NPC71520
0.875	High Similarity	NPC256567
0.875	High Similarity	NPC255882
0.8718	High Similarity	NPC102253
0.8718	High Similarity	NPC13554
0.8718	High Similarity	NPC47149
0.8718	High Similarity	NPC236237
0.8718	High Similarity	NPC322313
0.8701	High Similarity	NPC102708
0.8701	High Similarity	NPC475
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC167037
0.8701	High Similarity	NPC472502
0.8684	High Similarity	NPC63958
0.8684	High Similarity	NPC237460
0.8675	High Similarity	NPC74258
0.8667	High Similarity	NPC476736
0.8642	High Similarity	NPC470360
0.8625	High Similarity	NPC477818
0.8625	High Similarity	NPC110778
0.8611	High Similarity	NPC253303
0.8611	High Similarity	NPC269077
0.859	High Similarity	NPC472463
0.8571	High Similarity	NPC138502
0.8571	High Similarity	NPC46758
0.8571	High Similarity	NPC10274
0.8537	High Similarity	NPC299068
0.8537	High Similarity	NPC6391
0.8519	High Similarity	NPC299963
0.8519	High Similarity	NPC474493
0.8519	High Similarity	NPC209802
0.8514	High Similarity	NPC283316
0.85	High Similarity	NPC296701
0.85	High Similarity	NPC218616
0.85	High Similarity	NPC248886
0.85	High Similarity	NPC30166
0.85	High Similarity	NPC472504
0.8481	Intermediate Similarity	NPC206735
0.8471	Intermediate Similarity	NPC219516
0.8462	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC65897
0.8462	Intermediate Similarity	NPC302041
0.8462	Intermediate Similarity	NPC85346
0.8452	Intermediate Similarity	NPC101886
0.8452	Intermediate Similarity	NPC470361
0.8452	Intermediate Similarity	NPC109744
0.8442	Intermediate Similarity	NPC73875
0.8442	Intermediate Similarity	NPC189883
0.8442	Intermediate Similarity	NPC38141
0.8421	Intermediate Similarity	NPC192501
0.8421	Intermediate Similarity	NPC10476
0.8421	Intermediate Similarity	NPC304499
0.8421	Intermediate Similarity	NPC228994
0.8395	Intermediate Similarity	NPC207013
0.8395	Intermediate Similarity	NPC141941
0.8395	Intermediate Similarity	NPC193870
0.8378	Intermediate Similarity	NPC66407
0.8378	Intermediate Similarity	NPC254037
0.8378	Intermediate Similarity	NPC210323
0.8378	Intermediate Similarity	NPC129829
0.8375	Intermediate Similarity	NPC242350
0.8375	Intermediate Similarity	NPC157655
0.8354	Intermediate Similarity	NPC5604
0.8354	Intermediate Similarity	NPC1319
0.8353	Intermediate Similarity	NPC329596
0.8353	Intermediate Similarity	NPC11216
0.8353	Intermediate Similarity	NPC3345
0.8353	Intermediate Similarity	NPC475751
0.8353	Intermediate Similarity	NPC291484
0.8353	Intermediate Similarity	NPC80561
0.8353	Intermediate Similarity	NPC473956
0.8353	Intermediate Similarity	NPC204188
0.8333	Intermediate Similarity	NPC212596
0.8333	Intermediate Similarity	NPC300442
0.8333	Intermediate Similarity	NPC27243
0.8333	Intermediate Similarity	NPC318495
0.8333	Intermediate Similarity	NPC4574
0.8333	Intermediate Similarity	NPC476737
0.8333	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC193360
0.8333	Intermediate Similarity	NPC198968
0.8333	Intermediate Similarity	NPC214570
0.8313	Intermediate Similarity	NPC261266
0.8313	Intermediate Similarity	NPC94462
0.8313	Intermediate Similarity	NPC24277
0.8312	Intermediate Similarity	NPC257347
0.8312	Intermediate Similarity	NPC196136
0.8312	Intermediate Similarity	NPC243027
0.8312	Intermediate Similarity	NPC141071
0.8312	Intermediate Similarity	NPC121744
0.8312	Intermediate Similarity	NPC322353
0.8312	Intermediate Similarity	NPC471723
0.8312	Intermediate Similarity	NPC118508
0.8312	Intermediate Similarity	NPC158208
0.8293	Intermediate Similarity	NPC475798
0.8293	Intermediate Similarity	NPC124172
0.8293	Intermediate Similarity	NPC127606
0.8289	Intermediate Similarity	NPC211009
0.8289	Intermediate Similarity	NPC472506
0.8272	Intermediate Similarity	NPC477599
0.8267	Intermediate Similarity	NPC192192
0.8256	Intermediate Similarity	NPC41554
0.8256	Intermediate Similarity	NPC275671
0.8256	Intermediate Similarity	NPC97404
0.825	Intermediate Similarity	NPC236112
0.825	Intermediate Similarity	NPC26117
0.8243	Intermediate Similarity	NPC245795
0.8243	Intermediate Similarity	NPC266578
0.8243	Intermediate Similarity	NPC474756
0.8243	Intermediate Similarity	NPC2648
0.8228	Intermediate Similarity	NPC312328
0.8228	Intermediate Similarity	NPC148977
0.8228	Intermediate Similarity	NPC275910
0.8214	Intermediate Similarity	NPC475313
0.8214	Intermediate Similarity	NPC304083
0.8214	Intermediate Similarity	NPC186145
0.8214	Intermediate Similarity	NPC474657
0.8205	Intermediate Similarity	NPC46160
0.8205	Intermediate Similarity	NPC107059
0.8205	Intermediate Similarity	NPC134330
0.8205	Intermediate Similarity	NPC240604
0.8205	Intermediate Similarity	NPC321381
0.8205	Intermediate Similarity	NPC300324
0.8205	Intermediate Similarity	NPC321016

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 NPC31828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2549
0.2-0.3	4291
0.3-0.4	1490
0.4-0.5	273
0.5-0.6	143
0.6-0.7	171
0.7-0.8	63
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD7525	Registered
0.8133	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7339	Approved
0.8077	Intermediate Similarity	NPD6942	Approved
0.8025	Intermediate Similarity	NPD6931	Approved
0.8025	Intermediate Similarity	NPD6930	Phase 2
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7645	Phase 2
0.7901	Intermediate Similarity	NPD6929	Approved
0.7875	Intermediate Similarity	NPD6932	Approved
0.775	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6695	Phase 3
0.7722	Intermediate Similarity	NPD6924	Approved
0.7722	Intermediate Similarity	NPD6926	Approved
0.7683	Intermediate Similarity	NPD6683	Phase 2
0.7654	Intermediate Similarity	NPD6925	Approved
0.7654	Intermediate Similarity	NPD5776	Phase 2
0.7647	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7514	Phase 3
0.7586	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4787	Phase 1
0.7561	Intermediate Similarity	NPD7145	Approved
0.7558	Intermediate Similarity	NPD6893	Approved
0.7531	Intermediate Similarity	NPD6933	Approved
0.7529	Intermediate Similarity	NPD4788	Approved
0.7468	Intermediate Similarity	NPD4243	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7416	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD7524	Approved
0.7386	Intermediate Similarity	NPD7750	Discontinued
0.7381	Intermediate Similarity	NPD7332	Phase 2
0.7381	Intermediate Similarity	NPD4748	Discontinued
0.7349	Intermediate Similarity	NPD6697	Approved
0.7349	Intermediate Similarity	NPD6118	Approved
0.7349	Intermediate Similarity	NPD6115	Approved
0.7349	Intermediate Similarity	NPD6114	Approved
0.7294	Intermediate Similarity	NPD6902	Approved
0.7294	Intermediate Similarity	NPD6898	Phase 1
0.7284	Intermediate Similarity	NPD4784	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7253	Intermediate Similarity	NPD8035	Phase 2
0.7253	Intermediate Similarity	NPD8034	Phase 2
0.7253	Intermediate Similarity	NPD6079	Approved
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7152	Approved
0.725	Intermediate Similarity	NPD7150	Approved
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7151	Approved
0.7215	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD6923	Approved
0.7209	Intermediate Similarity	NPD3667	Approved
0.7195	Intermediate Similarity	NPD3703	Phase 2
0.7176	Intermediate Similarity	NPD7509	Discontinued
0.7174	Intermediate Similarity	NPD4202	Approved
0.7158	Intermediate Similarity	NPD7638	Approved
0.7125	Intermediate Similarity	NPD7144	Approved
0.7125	Intermediate Similarity	NPD7143	Approved
0.7108	Intermediate Similarity	NPD6117	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7087	Discontinued
0.7053	Intermediate Similarity	NPD4755	Approved
0.7024	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5275	Approved
0.6988	Remote Similarity	NPD4190	Phase 3
0.6977	Remote Similarity	NPD6928	Phase 2
0.6907	Remote Similarity	NPD4696	Approved
0.6907	Remote Similarity	NPD5285	Approved
0.6907	Remote Similarity	NPD5286	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD5360	Phase 3
0.6875	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4195	Approved
0.6854	Remote Similarity	NPD3666	Approved
0.6854	Remote Similarity	NPD3133	Approved
0.6854	Remote Similarity	NPD3665	Phase 1
0.6848	Remote Similarity	NPD4753	Phase 2
0.6771	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD5225	Approved
0.6768	Remote Similarity	NPD5226	Approved
0.6768	Remote Similarity	NPD4633	Approved
0.6768	Remote Similarity	NPD5224	Approved
0.6744	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6402	Approved
0.6733	Remote Similarity	NPD7128	Approved
0.6733	Remote Similarity	NPD5739	Approved
0.6733	Remote Similarity	NPD6675	Approved
0.6707	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6707	Remote Similarity	NPD4789	Approved
0.6702	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD5173	Approved
0.67	Remote Similarity	NPD5174	Approved
0.67	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6635	Remote Similarity	NPD4634	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6632	Remote Similarity	NPD6399	Phase 3
0.6629	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.6606	Remote Similarity	NPD7516	Approved
0.6602	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.6593	Remote Similarity	NPD5329	Approved
0.6585	Remote Similarity	NPD3698	Phase 2
0.6569	Remote Similarity	NPD4767	Approved
0.6569	Remote Similarity	NPD4768	Approved
0.6538	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD6373	Approved
0.6535	Remote Similarity	NPD4754	Approved
0.6531	Remote Similarity	NPD6084	Phase 2
0.6531	Remote Similarity	NPD6083	Phase 2
0.6526	Remote Similarity	NPD7637	Suspended
0.6522	Remote Similarity	NPD5279	Phase 3
0.6505	Remote Similarity	NPD5701	Approved
0.6505	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4159	Approved
0.6495	Remote Similarity	NPD4629	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6486	Remote Similarity	NPD8378	Approved
0.6486	Remote Similarity	NPD8380	Approved
0.6486	Remote Similarity	NPD8296	Approved
0.6486	Remote Similarity	NPD8379	Approved
0.6486	Remote Similarity	NPD8335	Approved
0.6484	Remote Similarity	NPD4197	Approved
0.6484	Remote Similarity	NPD3668	Phase 3
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6465	Remote Similarity	NPD5290	Discontinued
0.6449	Remote Similarity	NPD8133	Approved
0.6442	Remote Similarity	NPD4730	Approved
0.6442	Remote Similarity	NPD5128	Approved
0.6442	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4758	Discontinued
0.6421	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7136	Phase 2
0.6421	Remote Similarity	NPD6700	Approved
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD8294	Approved
0.6396	Remote Similarity	NPD8377	Approved
0.6395	Remote Similarity	NPD8264	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6381	Remote Similarity	NPD6012	Approved
0.6381	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD6014	Approved
0.6375	Remote Similarity	NPD371	Approved
0.6364	Remote Similarity	NPD3671	Phase 1
0.6355	Remote Similarity	NPD8297	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6354	Remote Similarity	NPD6702	Approved
0.6354	Remote Similarity	NPD6703	Approved
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4138	Approved
0.6344	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6344	Remote Similarity	NPD5205	Approved
0.6344	Remote Similarity	NPD4689	Approved
0.6339	Remote Similarity	NPD8033	Approved
0.6321	Remote Similarity	NPD5250	Approved
0.6321	Remote Similarity	NPD5247	Approved
0.6321	Remote Similarity	NPD5251	Approved
0.6321	Remote Similarity	NPD5249	Phase 3
0.6321	Remote Similarity	NPD5248	Approved
0.6316	Remote Similarity	NPD6051	Approved
0.6296	Remote Similarity	NPD4632	Approved
0.6289	Remote Similarity	NPD8171	Discontinued
0.6286	Remote Similarity	NPD6011	Approved
0.6265	Remote Similarity	NPD6705	Phase 1
0.6262	Remote Similarity	NPD5217	Approved
0.6262	Remote Similarity	NPD5216	Approved
0.6262	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6059	Approved
0.6211	Remote Similarity	NPD4722	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4723	Approved
0.62	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD6412	Phase 2
0.618	Remote Similarity	NPD3617	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