NPASS Compound

Structure

NPC8004 OpenBabel07101719142D 33 37 0 0 1 0 0 0 0 0999 V2000 -6.3604 1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2699 3.8576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0620 2.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 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 -4.9179 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4696 2.1045 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7206 2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6987 2.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 2.9781 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 -4.3301 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 -6.0514 1.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0733 2.1691 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 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3678 3.2396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3189 3.5486 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 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5757 4.2177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 7 28 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 32 1 0 0 0 0 20 1 1 1 0 0 0 20 21 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 1 0 0 0 23 30 1 0 0 0 0 24 12 1 1 0 0 0 24 25 1 0 0 0 0 24 33 1 0 0 0 0 25 33 1 0 0 0 0 26 31 1 0 0 0 0 27 6 1 1 0 0 0 28 29 1 6 0 0 0 29 8 1 1 0 0 0 30 26 1 6 0 0 0 30 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	511.024
LogP:	6.231
LogD:	4.67
LogS:	-5.202
# Rotatable Bonds:	5
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	5.046
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.755
MDCK Permeability:	9.602550562703982e-06
Pgp-inhibitor:	0.828
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	94.98790740966797%
Volume Distribution (VD):	1.156
Pgp-substrate:	2.0904834270477295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.625

ADMET: Excretion

Clearance (CL):	8.354
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.897
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.267
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.593
Skin Sensitization:	0.95
Carcinogencity:	0.383
Eye Corrosion:	0.219
Eye Irritation:	0.086
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC8004

Natural Product ID:	NPC8004
*Common Name:**	24S-4-Hydroxy-3,4-Seco-19(10->9)-Abeo-8Alpha,9Beta,10Alpha-Tirucallane-3,5Beta:24,25-Dioxide
IUPAC Name:	2-[(1S,3aR,3bS,5aR,9aS,9bR,11aS)-1-[(2S)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-3a,9b,11a-trimethyl-1,2,3,3b,4,5,7,8,9,9a,10,11-dodecahydroindeno[5,4-f]chromen-5a-yl]propan-2-ol
Synonyms:	(24S)-24,25-Epoxysunpollenol
Standard InCHIKey:	WWWOCVBEDWYMAJ-YTXZDOLYSA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-20(11-12-24-25(2,3)33-24)21-13-15-29(8)22-14-16-30(26(4,5)31)23(10-9-19-32-30)27(22,6)17-18-28(21,29)7/h20-24,31H,9-19H2,1-8H3/t20-,21-,22-,23-,24-,27+,28-,29+,30+/m0/s1
SMILES:	C[C@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@@]1([C@@H]2CC[C@@]2([C@H]1CCCO2)C(O)(C)C)C)C)CC[C@@H]1OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460759
PubChem CID:	10367015
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002382] Oxasteroids 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
NPO33432	sunflower pollen	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[14640522]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[565835]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[565835]
NPT2	Others	Unspecified		Activity	=	27.3	%	PMID[565835]
NPT2	Others	Unspecified		Activity	=	75.9	%	PMID[565835]
NPT2	Others	Unspecified		Activity	=	97.4	%	PMID[565835]

☑ 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 NPC8004 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	404
0.1-0.2	4468
0.2-0.3	16421
0.3-0.4	9187
0.4-0.5	4916
0.5-0.6	4853
0.6-0.7	1883
0.7-0.8	443
0.8-0.85	91
0.85-0.9	19
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC127283
0.9412	High Similarity	NPC157777
0.9412	High Similarity	NPC131506
0.9155	High Similarity	NPC470145
0.9	High Similarity	NPC472341
0.9	High Similarity	NPC473238
0.8857	High Similarity	NPC195530
0.8857	High Similarity	NPC473279
0.8841	High Similarity	NPC241085
0.8841	High Similarity	NPC470830
0.8841	High Similarity	NPC299948
0.875	High Similarity	NPC231680
0.875	High Similarity	NPC91387
0.875	High Similarity	NPC270306
0.8714	High Similarity	NPC282454
0.8667	High Similarity	NPC16449
0.8592	High Similarity	NPC100586
0.8592	High Similarity	NPC109457
0.8592	High Similarity	NPC157422
0.8571	High Similarity	NPC107919
0.8514	High Similarity	NPC474574
0.8514	High Similarity	NPC64081
0.8514	High Similarity	NPC133596
0.8514	High Similarity	NPC11907
0.8451	Intermediate Similarity	NPC231945
0.8356	Intermediate Similarity	NPC477508
0.8289	Intermediate Similarity	NPC477282
0.8289	Intermediate Similarity	NPC81074
0.8286	Intermediate Similarity	NPC475884
0.8286	Intermediate Similarity	NPC48079
0.8286	Intermediate Similarity	NPC473230
0.8286	Intermediate Similarity	NPC63190
0.8267	Intermediate Similarity	NPC476233
0.8261	Intermediate Similarity	NPC474380
0.8261	Intermediate Similarity	NPC41577
0.8261	Intermediate Similarity	NPC473276
0.8243	Intermediate Similarity	NPC472950
0.8243	Intermediate Similarity	NPC472952
0.8235	Intermediate Similarity	NPC114891
0.8219	Intermediate Similarity	NPC153719
0.8205	Intermediate Similarity	NPC475388
0.8169	Intermediate Similarity	NPC472741
0.8158	Intermediate Similarity	NPC471769
0.8143	Intermediate Similarity	NPC142712
0.8116	Intermediate Similarity	NPC69149
0.8108	Intermediate Similarity	NPC192501
0.8108	Intermediate Similarity	NPC10476
0.8108	Intermediate Similarity	NPC228994
0.8088	Intermediate Similarity	NPC148174
0.8088	Intermediate Similarity	NPC71460
0.8088	Intermediate Similarity	NPC218585
0.8082	Intermediate Similarity	NPC187471
0.8082	Intermediate Similarity	NPC252182
0.8082	Intermediate Similarity	NPC1340
0.8082	Intermediate Similarity	NPC470071
0.8077	Intermediate Similarity	NPC70927
0.8077	Intermediate Similarity	NPC190940
0.806	Intermediate Similarity	NPC95958
0.8056	Intermediate Similarity	NPC254037
0.8056	Intermediate Similarity	NPC66407
0.8056	Intermediate Similarity	NPC129829
0.8026	Intermediate Similarity	NPC171658
0.8025	Intermediate Similarity	NPC125399
0.8	Intermediate Similarity	NPC475943
0.8	Intermediate Similarity	NPC158208
0.8	Intermediate Similarity	NPC243027
0.8	Intermediate Similarity	NPC243469
0.8	Intermediate Similarity	NPC472946
0.8	Intermediate Similarity	NPC196136
0.8	Intermediate Similarity	NPC190827
0.8	Intermediate Similarity	NPC186851
0.8	Intermediate Similarity	NPC260116
0.8	Intermediate Similarity	NPC317242
0.7975	Intermediate Similarity	NPC286719
0.7975	Intermediate Similarity	NPC477286
0.7973	Intermediate Similarity	NPC470610
0.7945	Intermediate Similarity	NPC192192
0.7922	Intermediate Similarity	NPC147993
0.7901	Intermediate Similarity	NPC290612
0.7895	Intermediate Similarity	NPC163597
0.7895	Intermediate Similarity	NPC470766
0.7895	Intermediate Similarity	NPC91573
0.7887	Intermediate Similarity	NPC44122
0.7875	Intermediate Similarity	NPC477285
0.7875	Intermediate Similarity	NPC111582
0.7875	Intermediate Similarity	NPC470070
0.7867	Intermediate Similarity	NPC472944
0.7867	Intermediate Similarity	NPC48795
0.7867	Intermediate Similarity	NPC472945
0.7867	Intermediate Similarity	NPC272359
0.7857	Intermediate Similarity	NPC281540
0.7857	Intermediate Similarity	NPC159654
0.7857	Intermediate Similarity	NPC167995
0.7857	Intermediate Similarity	NPC118937
0.7838	Intermediate Similarity	NPC127094
0.7826	Intermediate Similarity	NPC185547
0.7826	Intermediate Similarity	NPC95804
0.7821	Intermediate Similarity	NPC287452
0.7808	Intermediate Similarity	NPC477820
0.7792	Intermediate Similarity	NPC302578
0.7792	Intermediate Similarity	NPC212453
0.7792	Intermediate Similarity	NPC185915
0.7792	Intermediate Similarity	NPC105208
0.7792	Intermediate Similarity	NPC128951
0.7792	Intermediate Similarity	NPC477227
0.7792	Intermediate Similarity	NPC192046
0.7778	Intermediate Similarity	NPC15534
0.7761	Intermediate Similarity	NPC135438
0.775	Intermediate Similarity	NPC60018
0.775	Intermediate Similarity	NPC154043
0.775	Intermediate Similarity	NPC202688
0.7738	Intermediate Similarity	NPC228059
0.7722	Intermediate Similarity	NPC472943
0.7722	Intermediate Similarity	NPC472951
0.7711	Intermediate Similarity	NPC43912
0.7711	Intermediate Similarity	NPC140446
0.7711	Intermediate Similarity	NPC202937
0.7703	Intermediate Similarity	NPC232925
0.7703	Intermediate Similarity	NPC251201
0.7703	Intermediate Similarity	NPC63588
0.7692	Intermediate Similarity	NPC18857
0.7692	Intermediate Similarity	NPC67657
0.7671	Intermediate Similarity	NPC474756
0.7671	Intermediate Similarity	NPC475893
0.7662	Intermediate Similarity	NPC477602
0.7662	Intermediate Similarity	NPC473916
0.7662	Intermediate Similarity	NPC477601
0.7654	Intermediate Similarity	NPC472744
0.7654	Intermediate Similarity	NPC132635
0.7647	Intermediate Similarity	NPC476735
0.7632	Intermediate Similarity	NPC478130
0.7632	Intermediate Similarity	NPC304499
0.7625	Intermediate Similarity	NPC77311
0.7625	Intermediate Similarity	NPC12933
0.7625	Intermediate Similarity	NPC473257
0.76	Intermediate Similarity	NPC478103
0.7595	Intermediate Similarity	NPC269333
0.7595	Intermediate Similarity	NPC245029
0.7595	Intermediate Similarity	NPC476176
0.7595	Intermediate Similarity	NPC31302
0.7595	Intermediate Similarity	NPC220379
0.759	Intermediate Similarity	NPC103782
0.759	Intermediate Similarity	NPC471240
0.759	Intermediate Similarity	NPC215968
0.759	Intermediate Similarity	NPC155531
0.759	Intermediate Similarity	NPC114378
0.759	Intermediate Similarity	NPC80700
0.759	Intermediate Similarity	NPC477283
0.7586	Intermediate Similarity	NPC30687
0.7568	Intermediate Similarity	NPC470833
0.7568	Intermediate Similarity	NPC99264
0.7564	Intermediate Similarity	NPC475031
0.7561	Intermediate Similarity	NPC474156
0.7561	Intermediate Similarity	NPC86238
0.7561	Intermediate Similarity	NPC320824
0.7558	Intermediate Similarity	NPC59006
0.7536	Intermediate Similarity	NPC185116
0.7534	Intermediate Similarity	NPC204233
0.7532	Intermediate Similarity	NPC70982
0.7532	Intermediate Similarity	NPC273366
0.7532	Intermediate Similarity	NPC230704
0.7532	Intermediate Similarity	NPC3403
0.7531	Intermediate Similarity	NPC470611
0.7529	Intermediate Similarity	NPC82955
0.7529	Intermediate Similarity	NPC131466
0.75	Intermediate Similarity	NPC206735
0.75	Intermediate Similarity	NPC117137
0.75	Intermediate Similarity	NPC210658
0.75	Intermediate Similarity	NPC232112
0.75	Intermediate Similarity	NPC80463
0.75	Intermediate Similarity	NPC236588
0.75	Intermediate Similarity	NPC253805
0.75	Intermediate Similarity	NPC161928
0.75	Intermediate Similarity	NPC66766
0.75	Intermediate Similarity	NPC13554
0.747	Intermediate Similarity	NPC273290
0.747	Intermediate Similarity	NPC232044
0.747	Intermediate Similarity	NPC266651
0.7468	Intermediate Similarity	NPC177343
0.7468	Intermediate Similarity	NPC471045
0.7468	Intermediate Similarity	NPC102708
0.7468	Intermediate Similarity	NPC472342
0.7468	Intermediate Similarity	NPC137587
0.7465	Intermediate Similarity	NPC236099
0.7465	Intermediate Similarity	NPC209686
0.7465	Intermediate Similarity	NPC249078
0.7442	Intermediate Similarity	NPC279329
0.7439	Intermediate Similarity	NPC259173
0.7416	Intermediate Similarity	NPC252056
0.7412	Intermediate Similarity	NPC128475
0.7412	Intermediate Similarity	NPC201607
0.7412	Intermediate Similarity	NPC473436
0.7412	Intermediate Similarity	NPC281004
0.7412	Intermediate Similarity	NPC56777
0.7407	Intermediate Similarity	NPC73515
0.7407	Intermediate Similarity	NPC58631
0.7403	Intermediate Similarity	NPC5046
0.7403	Intermediate Similarity	NPC254509
0.7403	Intermediate Similarity	NPC470151
0.7403	Intermediate Similarity	NPC196358

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 NPC8004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	4313
0.2-0.3	3162
0.3-0.4	758
0.4-0.5	206
0.5-0.6	247
0.6-0.7	40
0.7-0.8	19
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4267	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4787	Phase 1
0.7368	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6928	Phase 2
0.7215	Intermediate Similarity	NPD6117	Approved
0.72	Intermediate Similarity	NPD5360	Phase 3
0.72	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6116	Phase 1
0.7123	Intermediate Similarity	NPD371	Approved
0.7105	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3702	Approved
0.7073	Intermediate Similarity	NPD7525	Registered
0.7037	Intermediate Similarity	NPD6697	Approved
0.7037	Intermediate Similarity	NPD6115	Approved
0.7037	Intermediate Similarity	NPD6118	Approved
0.7037	Intermediate Similarity	NPD6114	Approved
0.6889	Remote Similarity	NPD8171	Discontinued
0.6875	Remote Similarity	NPD3703	Phase 2
0.68	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4245	Approved
0.6795	Remote Similarity	NPD4244	Approved
0.6795	Remote Similarity	NPD4789	Approved
0.6709	Remote Similarity	NPD4758	Discontinued
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6585	Remote Similarity	NPD6933	Approved
0.6562	Remote Similarity	NPD4159	Approved
0.6538	Remote Similarity	NPD6705	Phase 1
0.65	Remote Similarity	NPD5777	Approved
0.6477	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4748	Discontinued
0.6429	Remote Similarity	NPD5364	Discontinued
0.6429	Remote Similarity	NPD3671	Phase 1
0.6413	Remote Similarity	NPD8034	Phase 2
0.6413	Remote Similarity	NPD8035	Phase 2
0.6386	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7645	Phase 2
0.6341	Remote Similarity	NPD1811	Approved
0.6341	Remote Similarity	NPD6926	Approved
0.6341	Remote Similarity	NPD6924	Approved
0.6341	Remote Similarity	NPD1810	Approved
0.6333	Remote Similarity	NPD7524	Approved
0.6296	Remote Similarity	NPD4243	Approved
0.6296	Remote Similarity	NPD6081	Approved
0.6282	Remote Similarity	NPD4224	Phase 2
0.6269	Remote Similarity	NPD385	Approved
0.6269	Remote Similarity	NPD384	Approved
0.6222	Remote Similarity	NPD8308	Discontinued
0.62	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5328	Approved
0.618	Remote Similarity	NPD4786	Approved
0.6173	Remote Similarity	NPD2686	Approved
0.6173	Remote Similarity	NPD2687	Approved
0.6173	Remote Similarity	NPD2254	Approved
0.6145	Remote Similarity	NPD4784	Approved
0.6145	Remote Similarity	NPD4785	Approved
0.6129	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6700	Approved
0.6067	Remote Similarity	NPD4788	Approved
0.6067	Remote Similarity	NPD6695	Phase 3
0.6064	Remote Similarity	NPD6703	Approved
0.6064	Remote Similarity	NPD6702	Approved
0.6064	Remote Similarity	NPD6079	Approved
0.6044	Remote Similarity	NPD3618	Phase 1
0.6042	Remote Similarity	NPD7991	Discontinued
0.6019	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5978	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3667	Approved
0.5909	Remote Similarity	NPD7509	Discontinued
0.5909	Remote Similarity	NPD6930	Phase 2
0.5909	Remote Similarity	NPD6931	Approved
0.5904	Remote Similarity	NPD7151	Approved
0.5904	Remote Similarity	NPD7152	Approved
0.5904	Remote Similarity	NPD7150	Approved
0.59	Remote Similarity	NPD1700	Approved
0.5889	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3669	Approved
0.5882	Remote Similarity	NPD5275	Approved
0.5882	Remote Similarity	NPD386	Approved
0.5882	Remote Similarity	NPD388	Approved
0.5882	Remote Similarity	NPD4190	Phase 3
0.5859	Remote Similarity	NPD7638	Approved
0.5854	Remote Similarity	NPD6923	Approved
0.5854	Remote Similarity	NPD6922	Approved
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD6920	Discontinued
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD6675	Approved
0.5821	Remote Similarity	NPD367	Approved
0.5818	Remote Similarity	NPD7327	Approved
0.5818	Remote Similarity	NPD7328	Approved
0.581	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7750	Discontinued
0.58	Remote Similarity	NPD7639	Approved
0.58	Remote Similarity	NPD7640	Approved
0.5795	Remote Similarity	NPD6929	Approved
0.5795	Remote Similarity	NPD4195	Approved
0.5794	Remote Similarity	NPD8297	Approved
0.5783	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD7143	Approved
0.5783	Remote Similarity	NPD7144	Approved
0.5766	Remote Similarity	NPD7516	Approved
0.5758	Remote Similarity	NPD4755	Approved
0.5758	Remote Similarity	NPD7920	Phase 3
0.5758	Remote Similarity	NPD7919	Phase 3
0.5747	Remote Similarity	NPD6932	Approved
0.5741	Remote Similarity	NPD8133	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.57	Remote Similarity	NPD8088	Phase 1
0.5686	Remote Similarity	NPD7632	Discontinued
0.5684	Remote Similarity	NPD6051	Approved
0.5664	Remote Similarity	NPD8335	Approved
0.5664	Remote Similarity	NPD8380	Approved
0.5664	Remote Similarity	NPD8033	Approved
0.5664	Remote Similarity	NPD8296	Approved
0.5664	Remote Similarity	NPD8379	Approved
0.5664	Remote Similarity	NPD8378	Approved
0.566	Remote Similarity	NPD6372	Approved
0.566	Remote Similarity	NPD6373	Approved
0.5657	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4697	Phase 3
0.5657	Remote Similarity	NPD5222	Approved
0.5657	Remote Similarity	NPD5221	Approved
0.5652	Remote Similarity	NPD3133	Approved
0.5652	Remote Similarity	NPD3665	Phase 1
0.5652	Remote Similarity	NPD3666	Approved
0.5644	Remote Similarity	NPD8418	Phase 2
0.5644	Remote Similarity	NPD4700	Approved
0.5644	Remote Similarity	NPD5286	Approved
0.5644	Remote Similarity	NPD4696	Approved
0.5644	Remote Similarity	NPD5285	Approved
0.5636	Remote Similarity	NPD6940	Discontinued
0.5619	Remote Similarity	NPD5697	Approved
0.5619	Remote Similarity	NPD6412	Phase 2
0.5619	Remote Similarity	NPD5701	Approved
0.5618	Remote Similarity	NPD6683	Phase 2
0.5612	Remote Similarity	NPD7748	Approved
0.5607	Remote Similarity	NPD7102	Approved
0.5607	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7290	Approved
0.5607	Remote Similarity	NPD6883	Approved
0.5604	Remote Similarity	NPD4221	Approved
0.5604	Remote Similarity	NPD4223	Phase 3
0.56	Remote Similarity	NPD6083	Phase 2
0.56	Remote Similarity	NPD6084	Phase 2
0.56	Remote Similarity	NPD5173	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