NPASS Compound

Structure

NPC473257 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 -0.7857 1.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7349 2.2553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8064 2.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6573 3.5249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7810 2.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9985 0.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0822 0.5805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1002 -1.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1780 1.9046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0518 2.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 3.8024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6499 0.5805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 3.0693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0999 1.5171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7838 0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8142 1.5805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6969 -0.6461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5246 1.1476 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0427 0.2923 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9178 1.5805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3122 3.7277 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7477 -0.9608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6499 1.5805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5329 1.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8755 2.9014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7838 2.0805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0162 0.5206 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9178 0.5805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9099 -0.4149 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8142 0.5805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8122 4.5937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6194 -1.9525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3451 -0.4237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4178 -0.2855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5807 1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 8 29 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 20 26 1 6 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 29 1 6 0 0 0 22 32 1 0 0 0 0 23 26 1 6 0 0 0 23 35 1 0 0 0 0 24 30 1 0 0 0 0 25 35 1 0 0 0 0 26 5 1 6 0 0 0 27 6 1 1 0 0 0 27 33 1 0 0 0 0 28 7 1 1 0 0 0 28 34 1 0 0 0 0 29 30 1 1 0 0 0 29 36 1 0 0 0 0 30 16 1 1 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.38
Volume:	537.395
LogP:	3.849
LogD:	3.175
LogS:	-4.567
# Rotatable Bonds:	3
TPSA:	102.68
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	5.592
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
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:	-4.882
MDCK Permeability:	2.7386420697439462e-05
Pgp-inhibitor:	0.91
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.619

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	87.59192657470703%
Volume Distribution (VD):	0.94
Pgp-substrate:	10.200989723205566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.326
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	4.981
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.551
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.241
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC473257

Natural Product ID:	NPC473257
*Common Name:**	Sipholenol I
IUPAC Name:	(1aS,5R,7R,7aR)-1a-[2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepin-6-yl]ethyl]-2,2,5,7a-tetramethyl-2a,3,4,5a,6,7-hexahydroazuleno[5,6-b]oxirene-5,7-diol
Synonyms:	14Beta,15Beta-Epoxysipholenol E
Standard InCHIKey:	WWWZOBMNBOEYTA-NYKFADQYSA-N
Standard InCHI:	InChI=1S/C30H52O6/c1-24(2)18-9-14-27(6,33)19(18)17-22(32)29(8)30(24,36-29)16-10-20-26(5)13-11-21(31)25(3,4)35-23(26)12-15-28(20,7)34/h18-23,31-34H,9-17H2,1-8H3/t18?,19?,20-,21-,22-,23-,26-,27-,28+,29-,30+/m1/s1
SMILES:	CC1(C2CCC(C2CC(C3(C1(O3)CCC4C5(CCC(C(OC5CCC4(C)O)(C)C)O)C)C)O)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388090
PubChem CID:	16737095
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
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	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	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	8.6	nM	PMID[553003]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[553003]
NPT2	Others	Unspecified		IC50	=	2870.0	nM	PMID[553003]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[553003]

☑ 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 NPC473257 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	526
0.1-0.2	5164
0.2-0.3	15765
0.3-0.4	9509
0.4-0.5	6628
0.5-0.6	4306
0.6-0.7	716
0.7-0.8	76
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC66766
0.8861	High Similarity	NPC117137
0.825	Intermediate Similarity	NPC476233
0.8235	Intermediate Similarity	NPC64862
0.8228	Intermediate Similarity	NPC472952
0.8228	Intermediate Similarity	NPC131584
0.8228	Intermediate Similarity	NPC139765
0.8228	Intermediate Similarity	NPC472950
0.8193	Intermediate Similarity	NPC475388
0.8171	Intermediate Similarity	NPC16449
0.8125	Intermediate Similarity	NPC470145
0.8095	Intermediate Similarity	NPC29342
0.8095	Intermediate Similarity	NPC2572
0.8068	Intermediate Similarity	NPC470832
0.8	Intermediate Similarity	NPC474156
0.8	Intermediate Similarity	NPC317242
0.7901	Intermediate Similarity	NPC163597
0.7875	Intermediate Similarity	NPC475458
0.7867	Intermediate Similarity	NPC199937
0.7831	Intermediate Similarity	NPC477282
0.7831	Intermediate Similarity	NPC269333
0.7831	Intermediate Similarity	NPC287452
0.7831	Intermediate Similarity	NPC81074
0.7816	Intermediate Similarity	NPC471240
0.7805	Intermediate Similarity	NPC185915
0.7805	Intermediate Similarity	NPC477227
0.7805	Intermediate Similarity	NPC105208
0.7805	Intermediate Similarity	NPC302578
0.7805	Intermediate Similarity	NPC11907
0.7805	Intermediate Similarity	NPC128951
0.7805	Intermediate Similarity	NPC133596
0.7805	Intermediate Similarity	NPC192046
0.7805	Intermediate Similarity	NPC64081
0.7805	Intermediate Similarity	NPC474574
0.7802	Intermediate Similarity	NPC473258
0.7763	Intermediate Similarity	NPC165069
0.775	Intermediate Similarity	NPC470610
0.775	Intermediate Similarity	NPC153719
0.7738	Intermediate Similarity	NPC472943
0.7738	Intermediate Similarity	NPC472951
0.7727	Intermediate Similarity	NPC161928
0.7727	Intermediate Similarity	NPC472396
0.7727	Intermediate Similarity	NPC210658
0.7727	Intermediate Similarity	NPC5943
0.7711	Intermediate Similarity	NPC67657
0.7711	Intermediate Similarity	NPC147993
0.7711	Intermediate Similarity	NPC18857
0.7711	Intermediate Similarity	NPC471769
0.7701	Intermediate Similarity	NPC266651
0.7674	Intermediate Similarity	NPC69953
0.7674	Intermediate Similarity	NPC470070
0.7654	Intermediate Similarity	NPC48795
0.7654	Intermediate Similarity	NPC470151
0.7654	Intermediate Similarity	NPC304499
0.764	Intermediate Similarity	NPC128475
0.764	Intermediate Similarity	NPC22376
0.7625	Intermediate Similarity	NPC187471
0.7625	Intermediate Similarity	NPC470071
0.7625	Intermediate Similarity	NPC252182
0.7625	Intermediate Similarity	NPC8004
0.7625	Intermediate Similarity	NPC1340
0.7625	Intermediate Similarity	NPC131506
0.7625	Intermediate Similarity	NPC157777
0.7625	Intermediate Similarity	NPC127283
0.7614	Intermediate Similarity	NPC131365
0.7609	Intermediate Similarity	NPC76136
0.7609	Intermediate Similarity	NPC329713
0.7609	Intermediate Similarity	NPC217567
0.7609	Intermediate Similarity	NPC30687
0.759	Intermediate Similarity	NPC188793
0.7586	Intermediate Similarity	NPC320824
0.7582	Intermediate Similarity	NPC59006
0.7582	Intermediate Similarity	NPC473066
0.7561	Intermediate Similarity	NPC270306
0.7561	Intermediate Similarity	NPC196136
0.7561	Intermediate Similarity	NPC243027
0.7561	Intermediate Similarity	NPC231680
0.7561	Intermediate Similarity	NPC158208
0.7561	Intermediate Similarity	NPC91387
0.7558	Intermediate Similarity	NPC470611
0.7556	Intermediate Similarity	NPC228059
0.7529	Intermediate Similarity	NPC474714
0.75	Intermediate Similarity	NPC290612
0.75	Intermediate Similarity	NPC232925
0.75	Intermediate Similarity	NPC251201
0.75	Intermediate Similarity	NPC272841
0.75	Intermediate Similarity	NPC63588
0.7473	Intermediate Similarity	NPC279329
0.7471	Intermediate Similarity	NPC478054
0.7468	Intermediate Similarity	NPC474756
0.7444	Intermediate Similarity	NPC281004
0.7439	Intermediate Similarity	NPC228994
0.7439	Intermediate Similarity	NPC192501
0.7439	Intermediate Similarity	NPC10476
0.7419	Intermediate Similarity	NPC175
0.7416	Intermediate Similarity	NPC215968
0.7416	Intermediate Similarity	NPC472745
0.7416	Intermediate Similarity	NPC155531
0.7416	Intermediate Similarity	NPC145245
0.7412	Intermediate Similarity	NPC476176
0.7391	Intermediate Similarity	NPC36372
0.7391	Intermediate Similarity	NPC293609
0.7391	Intermediate Similarity	NPC210268
0.7386	Intermediate Similarity	NPC242016
0.7381	Intermediate Similarity	NPC476719
0.7375	Intermediate Similarity	NPC107919
0.7375	Intermediate Similarity	NPC477820
0.7375	Intermediate Similarity	NPC66407
0.7363	Intermediate Similarity	NPC102725
0.7363	Intermediate Similarity	NPC20822
0.7363	Intermediate Similarity	NPC473472
0.7356	Intermediate Similarity	NPC477446
0.7356	Intermediate Similarity	NPC202688
0.7356	Intermediate Similarity	NPC470155
0.7356	Intermediate Similarity	NPC60018
0.7356	Intermediate Similarity	NPC477447
0.7356	Intermediate Similarity	NPC154043
0.734	Intermediate Similarity	NPC473064
0.734	Intermediate Similarity	NPC473065
0.734	Intermediate Similarity	NPC473067
0.7333	Intermediate Similarity	NPC202937
0.7333	Intermediate Similarity	NPC43912
0.7333	Intermediate Similarity	NPC140446
0.7326	Intermediate Similarity	NPC186588
0.7317	Intermediate Similarity	NPC473238
0.7317	Intermediate Similarity	NPC472341
0.7312	Intermediate Similarity	NPC311246
0.7312	Intermediate Similarity	NPC256104
0.7312	Intermediate Similarity	NPC473726
0.7312	Intermediate Similarity	NPC277774
0.7312	Intermediate Similarity	NPC211845
0.7312	Intermediate Similarity	NPC182740
0.7312	Intermediate Similarity	NPC122083
0.7312	Intermediate Similarity	NPC167644
0.7308	Intermediate Similarity	NPC472946
0.7303	Intermediate Similarity	NPC273290
0.7303	Intermediate Similarity	NPC232044
0.7294	Intermediate Similarity	NPC471045
0.7283	Intermediate Similarity	NPC473542
0.7283	Intermediate Similarity	NPC65550
0.7283	Intermediate Similarity	NPC223143
0.7273	Intermediate Similarity	NPC477285
0.7273	Intermediate Similarity	NPC111582
0.7263	Intermediate Similarity	NPC142264
0.7263	Intermediate Similarity	NPC156377
0.7263	Intermediate Similarity	NPC476510
0.7262	Intermediate Similarity	NPC136424
0.7241	Intermediate Similarity	NPC470154
0.7241	Intermediate Similarity	NPC216941
0.7241	Intermediate Similarity	NPC470156
0.7234	Intermediate Similarity	NPC39453
0.7234	Intermediate Similarity	NPC309866
0.7234	Intermediate Similarity	NPC113500
0.7234	Intermediate Similarity	NPC3538
0.7234	Intermediate Similarity	NPC470424
0.7234	Intermediate Similarity	NPC45959
0.7234	Intermediate Similarity	NPC252253
0.7234	Intermediate Similarity	NPC477224
0.7234	Intermediate Similarity	NPC473503
0.7229	Intermediate Similarity	NPC472945
0.7229	Intermediate Similarity	NPC308489
0.7229	Intermediate Similarity	NPC472944
0.7222	Intermediate Similarity	NPC477283
0.7216	Intermediate Similarity	NPC470030
0.7204	Intermediate Similarity	NPC476668
0.7204	Intermediate Similarity	NPC473637
0.7204	Intermediate Similarity	NPC473830
0.7204	Intermediate Similarity	NPC5632
0.7204	Intermediate Similarity	NPC204881
0.7204	Intermediate Similarity	NPC149966
0.7195	Intermediate Similarity	NPC195530
0.7195	Intermediate Similarity	NPC109457
0.7195	Intermediate Similarity	NPC157422
0.7195	Intermediate Similarity	NPC127094
0.7195	Intermediate Similarity	NPC100586
0.7191	Intermediate Similarity	NPC86238
0.7191	Intermediate Similarity	NPC227260
0.7188	Intermediate Similarity	NPC470028
0.7188	Intermediate Similarity	NPC476040
0.7188	Intermediate Similarity	NPC474994
0.7188	Intermediate Similarity	NPC233649
0.7188	Intermediate Similarity	NPC476021
0.7179	Intermediate Similarity	NPC476702
0.7176	Intermediate Similarity	NPC171658
0.7174	Intermediate Similarity	NPC82955
0.7174	Intermediate Similarity	NPC131466
0.716	Intermediate Similarity	NPC241085
0.716	Intermediate Similarity	NPC299948
0.716	Intermediate Similarity	NPC470833
0.716	Intermediate Similarity	NPC470830
0.7159	Intermediate Similarity	NPC286719
0.7159	Intermediate Similarity	NPC477286
0.7159	Intermediate Similarity	NPC296734
0.7159	Intermediate Similarity	NPC475849
0.7158	Intermediate Similarity	NPC92196
0.7158	Intermediate Similarity	NPC17336
0.7158	Intermediate Similarity	NPC469710
0.7143	Intermediate Similarity	NPC95804
0.7143	Intermediate Similarity	NPC185547
0.7143	Intermediate Similarity	NPC186851

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 NPC473257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	619
0.1-0.2	4817
0.2-0.3	2636
0.3-0.4	617
0.4-0.5	305
0.5-0.6	150
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7375	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8171	Discontinued
0.6932	Remote Similarity	NPD6928	Phase 2
0.675	Remote Similarity	NPD371	Approved
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4787	Phase 1
0.6634	Remote Similarity	NPD1700	Approved
0.6437	Remote Similarity	NPD1810	Approved
0.6437	Remote Similarity	NPD1811	Approved
0.6333	Remote Similarity	NPD6118	Approved
0.6333	Remote Similarity	NPD6115	Approved
0.6333	Remote Similarity	NPD6114	Approved
0.6333	Remote Similarity	NPD6697	Approved
0.6286	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7524	Approved
0.6222	Remote Similarity	NPD6116	Phase 1
0.6196	Remote Similarity	NPD7525	Registered
0.6111	Remote Similarity	NPD6117	Approved
0.6105	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD2686	Approved
0.6092	Remote Similarity	NPD2687	Approved
0.6092	Remote Similarity	NPD2254	Approved
0.6053	Remote Similarity	NPD7328	Approved
0.6053	Remote Similarity	NPD7327	Approved
0.6023	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD3703	Phase 2
0.6	Remote Similarity	NPD4159	Approved
0.598	Remote Similarity	NPD7991	Discontinued
0.5909	Remote Similarity	NPD4244	Approved
0.5909	Remote Similarity	NPD4245	Approved
0.5909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4748	Discontinued
0.5849	Remote Similarity	NPD5344	Discontinued
0.5833	Remote Similarity	NPD3669	Approved
0.5833	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3702	Approved
0.5812	Remote Similarity	NPD8377	Approved
0.5812	Remote Similarity	NPD8294	Approved
0.5795	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3698	Phase 2
0.5795	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8378	Approved
0.5763	Remote Similarity	NPD8033	Approved
0.5763	Remote Similarity	NPD8379	Approved
0.5763	Remote Similarity	NPD8380	Approved
0.5763	Remote Similarity	NPD8296	Approved
0.5763	Remote Similarity	NPD8335	Approved
0.5761	Remote Similarity	NPD6933	Approved
0.5758	Remote Similarity	NPD7750	Discontinued
0.5743	Remote Similarity	NPD3168	Discontinued
0.5727	Remote Similarity	NPD6412	Phase 2
0.5702	Remote Similarity	NPD4632	Approved
0.5702	Remote Similarity	NPD8133	Approved
0.5698	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6931	Approved
0.5684	Remote Similarity	NPD6930	Phase 2
0.5682	Remote Similarity	NPD5360	Phase 3
0.5682	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6059	Approved
0.5678	Remote Similarity	NPD6054	Approved
0.5678	Remote Similarity	NPD6319	Approved
0.5676	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7638	Approved
0.5636	Remote Similarity	NPD7128	Approved
0.5636	Remote Similarity	NPD5739	Approved
0.5636	Remote Similarity	NPD6402	Approved
0.5636	Remote Similarity	NPD6675	Approved
0.563	Remote Similarity	NPD7503	Approved
0.5614	Remote Similarity	NPD8297	Approved
0.5607	Remote Similarity	NPD7640	Approved
0.5607	Remote Similarity	NPD7639	Approved
0.56	Remote Similarity	NPD4751	Clinical (unspecified phase)

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