NPASS Compound

Structure

NPC329713 OpenBabel07101718302D 36 40 0 0 1 0 0 0 0 0999 V2000 -0.0475 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6531 2.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8021 1.3623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5612 0.1344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8273 1.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1484 1.7933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7768 0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2569 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8003 2.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3107 2.6286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6147 -0.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8807 1.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6305 1.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.3614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6809 1.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3079 2.5539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2025 0.1386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8712 1.7277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8594 0.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6147 0.9476 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 0.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4899 2.4185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8079 3.4199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5765 0.7721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2015 0.0938 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 18 1 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 6 27 1 0 0 0 0 7 28 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 19 1 0 0 0 0 18 30 1 1 0 0 0 19 24 1 0 0 0 0 19 31 1 6 0 0 0 20 26 1 0 0 0 0 20 32 2 0 0 0 0 21 25 1 0 0 0 0 21 33 1 6 0 0 0 22 28 1 6 0 0 0 22 34 1 0 0 0 0 23 27 1 1 0 0 0 23 35 1 0 0 0 0 24 29 1 0 0 0 0 24 36 1 1 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 29 1 1 0 0 0 28 30 1 6 0 0 0 29 8 1 1 0 0 0 30 17 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.36
Volume:	534.759
LogP:	4.427
LogD:	3.378
LogS:	-3.242
# Rotatable Bonds:	1
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	5.883
Fsp3:	0.967
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:	-5.057
MDCK Permeability:	1.6531608707737178e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.377
Plasma Protein Binding (PPB):	64.56295013427734%
Volume Distribution (VD):	1.195
Pgp-substrate:	15.03111457824707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.494
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.751
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	9.773
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.345
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.624
Carcinogencity:	0.757
Eye Corrosion:	0.096
Eye Irritation:	0.023
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC329713

Natural Product ID:	NPC329713
*Common Name:**	Yardenone B
IUPAC Name:	(5aS,6S,8aS)-6-[(2'R,3R,3'S,5aR,6S,7S,9aS)-3,3'-dihydroxy-2,2,5a,7-tetramethylspiro[4,5,7,8,9,9a-hexahydro-3H-benzo[b]oxepine-6,5'-oxolane]-2'-yl]-2,2,5a,6-tetramethyl-5,7,8,8a-tetrahydro-4H-cyclopenta[b]oxepin-3-one
Synonyms:
Standard InCHIKey:	JFTRZCAXXYMBGB-OVSCOPMZSA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-18-9-10-22-28(7,15-12-21(33)25(2,3)34-22)30(18)17-19(31)24(36-30)29(8)16-13-23-27(29,6)14-11-20(32)26(4,5)35-23/h18-19,21-24,31,33H,9-17H2,1-8H3/t18-,19-,21+,22-,23-,24-,27+,28+,29+,30-/m0/s1
SMILES:	CC1CCC2C(C13CC(C(O3)C4(CCC5C4(CCC(=O)C(O5)(C)C)C)C)O)(CCC(C(O2)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514920
PubChem CID:	10051936
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
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[12542339]
NPO32762	axinella cf. bidderi	Species	Axinellidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[15043442]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	31000.0	nM	PMID[490194]

☑ 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 NPC329713 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	473
0.1-0.2	3865
0.2-0.3	10012
0.3-0.4	14064
0.4-0.5	7444
0.5-0.6	5637
0.6-0.7	1098
0.7-0.8	99
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76136
1.0	High Similarity	NPC217567
0.9195	High Similarity	NPC243746
0.8144	Intermediate Similarity	NPC476728
0.8144	Intermediate Similarity	NPC260223
0.8125	Intermediate Similarity	NPC470424
0.798	Intermediate Similarity	NPC211087
0.798	Intermediate Similarity	NPC253995
0.7957	Intermediate Similarity	NPC80700
0.7957	Intermediate Similarity	NPC476727
0.7957	Intermediate Similarity	NPC476726
0.7849	Intermediate Similarity	NPC476715
0.7789	Intermediate Similarity	NPC476435
0.7778	Intermediate Similarity	NPC116683
0.7742	Intermediate Similarity	NPC291310
0.7708	Intermediate Similarity	NPC61688
0.7677	Intermediate Similarity	NPC305808
0.7677	Intermediate Similarity	NPC17336
0.7634	Intermediate Similarity	NPC327451
0.7629	Intermediate Similarity	NPC477433
0.7629	Intermediate Similarity	NPC477442
0.7629	Intermediate Similarity	NPC477444
0.7624	Intermediate Similarity	NPC17183
0.7609	Intermediate Similarity	NPC473257
0.7604	Intermediate Similarity	NPC226491
0.7604	Intermediate Similarity	NPC477614
0.7604	Intermediate Similarity	NPC191221
0.7579	Intermediate Similarity	NPC476717
0.7579	Intermediate Similarity	NPC472745
0.7579	Intermediate Similarity	NPC474448
0.7551	Intermediate Similarity	NPC52756
0.7526	Intermediate Similarity	NPC477440
0.7526	Intermediate Similarity	NPC477443
0.7523	Intermediate Similarity	NPC97002
0.75	Intermediate Similarity	NPC239938
0.75	Intermediate Similarity	NPC473062
0.75	Intermediate Similarity	NPC263802
0.7476	Intermediate Similarity	NPC178853
0.7476	Intermediate Similarity	NPC298266
0.7476	Intermediate Similarity	NPC259654
0.7474	Intermediate Similarity	NPC477445
0.7455	Intermediate Similarity	NPC470115
0.7455	Intermediate Similarity	NPC470116
0.7451	Intermediate Similarity	NPC476294
0.7447	Intermediate Similarity	NPC227170
0.7429	Intermediate Similarity	NPC100078
0.7429	Intermediate Similarity	NPC473526
0.7429	Intermediate Similarity	NPC473701
0.7429	Intermediate Similarity	NPC88469
0.7429	Intermediate Similarity	NPC327093
0.7426	Intermediate Similarity	NPC477264
0.7419	Intermediate Similarity	NPC254123
0.7404	Intermediate Similarity	NPC213528
0.7404	Intermediate Similarity	NPC244969
0.7396	Intermediate Similarity	NPC472272
0.7396	Intermediate Similarity	NPC475729
0.7396	Intermediate Similarity	NPC474215
0.7387	Intermediate Similarity	NPC475490
0.7374	Intermediate Similarity	NPC216137
0.7374	Intermediate Similarity	NPC474065
0.7368	Intermediate Similarity	NPC50438
0.7368	Intermediate Similarity	NPC477434
0.7368	Intermediate Similarity	NPC475689
0.7358	Intermediate Similarity	NPC166079
0.7358	Intermediate Similarity	NPC168890
0.7353	Intermediate Similarity	NPC470834
0.734	Intermediate Similarity	NPC148740
0.734	Intermediate Similarity	NPC317066
0.734	Intermediate Similarity	NPC102156
0.7327	Intermediate Similarity	NPC62407
0.7327	Intermediate Similarity	NPC470031
0.7327	Intermediate Similarity	NPC287354
0.732	Intermediate Similarity	NPC202937
0.7315	Intermediate Similarity	NPC217041
0.73	Intermediate Similarity	NPC161035
0.73	Intermediate Similarity	NPC476189
0.7292	Intermediate Similarity	NPC473350
0.729	Intermediate Similarity	NPC176756
0.7273	Intermediate Similarity	NPC476296
0.7263	Intermediate Similarity	NPC268578
0.7263	Intermediate Similarity	NPC292458
0.7263	Intermediate Similarity	NPC69953
0.7263	Intermediate Similarity	NPC217559
0.7263	Intermediate Similarity	NPC2572
0.7263	Intermediate Similarity	NPC29342
0.7263	Intermediate Similarity	NPC476721
0.7248	Intermediate Similarity	NPC182185
0.7245	Intermediate Similarity	NPC471221
0.7238	Intermediate Similarity	NPC470840
0.7238	Intermediate Similarity	NPC470172
0.7228	Intermediate Similarity	NPC477495
0.7228	Intermediate Similarity	NPC470423
0.7228	Intermediate Similarity	NPC206878
0.7222	Intermediate Similarity	NPC316930
0.7222	Intermediate Similarity	NPC167044
0.7222	Intermediate Similarity	NPC220773
0.7222	Intermediate Similarity	NPC278693
0.7216	Intermediate Similarity	NPC215968
0.7216	Intermediate Similarity	NPC477441
0.7216	Intermediate Similarity	NPC92139
0.7216	Intermediate Similarity	NPC155531
0.7204	Intermediate Similarity	NPC477282
0.7204	Intermediate Similarity	NPC81074
0.7204	Intermediate Similarity	NPC245029
0.7204	Intermediate Similarity	NPC31302
0.72	Intermediate Similarity	NPC111883
0.72	Intermediate Similarity	NPC474699
0.7196	Intermediate Similarity	NPC306776
0.7196	Intermediate Similarity	NPC215408
0.7188	Intermediate Similarity	NPC105895
0.7184	Intermediate Similarity	NPC471241
0.717	Intermediate Similarity	NPC473406
0.717	Intermediate Similarity	NPC34562
0.717	Intermediate Similarity	NPC471253
0.7168	Intermediate Similarity	NPC179429
0.7158	Intermediate Similarity	NPC475388
0.7158	Intermediate Similarity	NPC100366
0.7158	Intermediate Similarity	NPC164289
0.7158	Intermediate Similarity	NPC311642
0.7158	Intermediate Similarity	NPC242771
0.7156	Intermediate Similarity	NPC321661
0.7156	Intermediate Similarity	NPC320475
0.7156	Intermediate Similarity	NPC227879
0.7156	Intermediate Similarity	NPC208333
0.7143	Intermediate Similarity	NPC5943
0.7143	Intermediate Similarity	NPC477172
0.713	Intermediate Similarity	NPC469787
0.713	Intermediate Similarity	NPC290247
0.713	Intermediate Similarity	NPC469788
0.713	Intermediate Similarity	NPC203974
0.7129	Intermediate Similarity	NPC474379
0.7128	Intermediate Similarity	NPC66766
0.7128	Intermediate Similarity	NPC117137
0.7128	Intermediate Similarity	NPC470609
0.7117	Intermediate Similarity	NPC98870
0.7115	Intermediate Similarity	NPC472144
0.7115	Intermediate Similarity	NPC274695
0.7113	Intermediate Similarity	NPC266651
0.7103	Intermediate Similarity	NPC470167
0.7103	Intermediate Similarity	NPC470838
0.71	Intermediate Similarity	NPC77756
0.71	Intermediate Similarity	NPC470114
0.7097	Intermediate Similarity	NPC252483
0.7097	Intermediate Similarity	NPC191345
0.7097	Intermediate Similarity	NPC478084
0.7087	Intermediate Similarity	NPC235109
0.7087	Intermediate Similarity	NPC163685
0.7087	Intermediate Similarity	NPC475785
0.7083	Intermediate Similarity	NPC15091
0.7075	Intermediate Similarity	NPC471254
0.7071	Intermediate Similarity	NPC470009
0.7071	Intermediate Similarity	NPC476379
0.7064	Intermediate Similarity	NPC472079
0.7064	Intermediate Similarity	NPC202898
0.7064	Intermediate Similarity	NPC475319
0.7064	Intermediate Similarity	NPC92890
0.7059	Intermediate Similarity	NPC247877
0.7059	Intermediate Similarity	NPC309127
0.7053	Intermediate Similarity	NPC469745
0.7053	Intermediate Similarity	NPC211049
0.7053	Intermediate Similarity	NPC77311
0.7048	Intermediate Similarity	NPC41843
0.7041	Intermediate Similarity	NPC235196
0.7041	Intermediate Similarity	NPC64862
0.7041	Intermediate Similarity	NPC131365
0.7041	Intermediate Similarity	NPC228593
0.7041	Intermediate Similarity	NPC477283
0.7037	Intermediate Similarity	NPC41674
0.7037	Intermediate Similarity	NPC228311
0.7037	Intermediate Similarity	NPC469441
0.7037	Intermediate Similarity	NPC50535
0.703	Intermediate Similarity	NPC473066
0.7027	Intermediate Similarity	NPC157476
0.7021	Intermediate Similarity	NPC275243
0.7019	Intermediate Similarity	NPC74466
0.7019	Intermediate Similarity	NPC472273
0.7019	Intermediate Similarity	NPC111187
0.7019	Intermediate Similarity	NPC190080
0.7019	Intermediate Similarity	NPC472145
0.7019	Intermediate Similarity	NPC470632
0.701	Intermediate Similarity	NPC474996
0.7009	Intermediate Similarity	NPC131824
0.7009	Intermediate Similarity	NPC107385
0.7009	Intermediate Similarity	NPC65858
0.7009	Intermediate Similarity	NPC470839
0.7	Intermediate Similarity	NPC56962
0.7	Intermediate Similarity	NPC273002
0.7	Intermediate Similarity	NPC228190
0.7	Intermediate Similarity	NPC92297
0.7	Intermediate Similarity	NPC200580
0.7	Intermediate Similarity	NPC236753
0.7	Intermediate Similarity	NPC220836
0.7	Intermediate Similarity	NPC233433
0.7	Intermediate Similarity	NPC94086
0.7	Intermediate Similarity	NPC24705
0.7	Intermediate Similarity	NPC473817
0.6991	Remote Similarity	NPC326542
0.699	Remote Similarity	NPC470191
0.699	Remote Similarity	NPC82633
0.6989	Remote Similarity	NPC474574

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 NPC329713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	583
0.1-0.2	4178
0.2-0.3	3043
0.3-0.4	785
0.4-0.5	319
0.5-0.6	192
0.6-0.7	49
0.7-0.8	1
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
0.7647	Intermediate Similarity	NPD1700	Approved
0.7264	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6054	Approved
0.6983	Remote Similarity	NPD6059	Approved
0.6957	Remote Similarity	NPD3703	Phase 2
0.6864	Remote Similarity	NPD6370	Approved
0.678	Remote Similarity	NPD6016	Approved
0.678	Remote Similarity	NPD6015	Approved
0.6757	Remote Similarity	NPD7320	Approved
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7492	Approved
0.6727	Remote Similarity	NPD6675	Approved
0.6727	Remote Similarity	NPD6402	Approved
0.6727	Remote Similarity	NPD7128	Approved
0.6727	Remote Similarity	NPD5739	Approved
0.6723	Remote Similarity	NPD5988	Approved
0.6695	Remote Similarity	NPD6319	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD7078	Approved
0.6636	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4632	Approved
0.6607	Remote Similarity	NPD6899	Approved
0.6607	Remote Similarity	NPD6881	Approved
0.6585	Remote Similarity	NPD7736	Approved
0.6562	Remote Similarity	NPD6118	Approved
0.6562	Remote Similarity	NPD6115	Approved
0.6562	Remote Similarity	NPD6697	Approved
0.6562	Remote Similarity	NPD6114	Approved
0.6549	Remote Similarity	NPD6373	Approved
0.6549	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD4244	Approved
0.6522	Remote Similarity	NPD4245	Approved
0.6518	Remote Similarity	NPD5697	Approved
0.6518	Remote Similarity	NPD5701	Approved
0.6491	Remote Similarity	NPD7102	Approved
0.6491	Remote Similarity	NPD7290	Approved
0.6491	Remote Similarity	NPD4634	Approved
0.6491	Remote Similarity	NPD6883	Approved
0.6458	Remote Similarity	NPD6116	Phase 1
0.6452	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6033	Approved
0.6441	Remote Similarity	NPD6009	Approved
0.6435	Remote Similarity	NPD6617	Approved
0.6435	Remote Similarity	NPD8130	Phase 1
0.6435	Remote Similarity	NPD6869	Approved
0.6435	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6435	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD5286	Approved
0.6422	Remote Similarity	NPD5285	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6422	Remote Similarity	NPD4696	Approved
0.6413	Remote Similarity	NPD3698	Phase 2
0.6413	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6012	Approved
0.6404	Remote Similarity	NPD6014	Approved
0.6404	Remote Similarity	NPD6013	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6379	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6354	Remote Similarity	NPD6117	Approved
0.6344	Remote Similarity	NPD4789	Approved
0.6321	Remote Similarity	NPD8171	Discontinued
0.6316	Remote Similarity	NPD6011	Approved
0.6306	Remote Similarity	NPD5225	Approved
0.6306	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD5226	Approved
0.6306	Remote Similarity	NPD5224	Approved
0.6306	Remote Similarity	NPD5211	Phase 2
0.6293	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6336	Discontinued
0.6263	Remote Similarity	NPD6928	Phase 2
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD3702	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6237	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD5223	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.616	Remote Similarity	NPD7507	Approved
0.6154	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7319	Approved
0.614	Remote Similarity	NPD6008	Approved
0.614	Remote Similarity	NPD4767	Approved
0.614	Remote Similarity	NPD4768	Approved
0.6129	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5360	Phase 3
0.6106	Remote Similarity	NPD4754	Approved
0.6105	Remote Similarity	NPD5777	Approved
0.6098	Remote Similarity	NPD6921	Approved
0.6091	Remote Similarity	NPD6084	Phase 2
0.6091	Remote Similarity	NPD6083	Phase 2
0.6083	Remote Similarity	NPD6274	Approved
0.6066	Remote Similarity	NPD7100	Approved
0.6066	Remote Similarity	NPD7101	Approved
0.6044	Remote Similarity	NPD371	Approved
0.6034	Remote Similarity	NPD4729	Approved
0.6034	Remote Similarity	NPD5128	Approved
0.6034	Remote Similarity	NPD4730	Approved
0.6033	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6335	Approved
0.5983	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6909	Approved
0.5968	Remote Similarity	NPD6908	Approved
0.5932	Remote Similarity	NPD5247	Approved
0.5932	Remote Similarity	NPD5249	Phase 3
0.5932	Remote Similarity	NPD5251	Approved
0.5932	Remote Similarity	NPD5248	Approved
0.5932	Remote Similarity	NPD5250	Approved
0.5917	Remote Similarity	NPD8133	Approved
0.5909	Remote Similarity	NPD5695	Phase 3
0.5902	Remote Similarity	NPD6317	Approved
0.59	Remote Similarity	NPD3671	Phase 1
0.59	Remote Similarity	NPD4802	Phase 2
0.59	Remote Similarity	NPD4238	Approved
0.5888	Remote Similarity	NPD5328	Approved
0.5888	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD1780	Approved
0.5882	Remote Similarity	NPD5216	Approved
0.5882	Remote Similarity	NPD1779	Approved
0.5882	Remote Similarity	NPD5217	Approved
0.5882	Remote Similarity	NPD5215	Approved
0.5873	Remote Similarity	NPD8328	Phase 3
0.5873	Remote Similarity	NPD6067	Discontinued
0.5872	Remote Similarity	NPD4202	Approved
0.5856	Remote Similarity	NPD5221	Approved
0.5856	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4697	Phase 3
0.5856	Remote Similarity	NPD5222	Approved
0.5854	Remote Similarity	NPD6314	Approved
0.5854	Remote Similarity	NPD6313	Approved
0.5847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.584	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6053	Discontinued
0.5825	Remote Similarity	NPD6435	Approved
0.5818	Remote Similarity	NPD5282	Discontinued
0.5812	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5173	Approved
0.5798	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD5135	Approved
0.5798	Remote Similarity	NPD5169	Approved
0.578	Remote Similarity	NPD8035	Phase 2
0.578	Remote Similarity	NPD6079	Approved
0.578	Remote Similarity	NPD8034	Phase 2
0.5778	Remote Similarity	NPD3198	Approved
0.5773	Remote Similarity	NPD4758	Discontinued
0.5769	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3669	Approved
0.5769	Remote Similarity	NPD4788	Approved
0.5752	Remote Similarity	NPD5696	Approved
0.5752	Remote Similarity	NPD7638	Approved
0.575	Remote Similarity	NPD5127	Approved
0.5743	Remote Similarity	NPD5364	Discontinued
0.5726	Remote Similarity	NPD7328	Approved
0.5726	Remote Similarity	NPD7327	Approved
0.5725	Remote Similarity	NPD5956	Approved
0.5702	Remote Similarity	NPD7639	Approved
0.5702	Remote Similarity	NPD7640	Approved
0.5691	Remote Similarity	NPD6940	Discontinued
0.568	Remote Similarity	NPD7516	Approved
0.567	Remote Similarity	NPD4787	Phase 1
0.5667	Remote Similarity	NPD6371	Approved
0.5667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD1811	Approved
0.5657	Remote Similarity	NPD1810	Approved
0.5631	Remote Similarity	NPD5368	Approved
0.5625	Remote Similarity	NPD4629	Approved
0.5625	Remote Similarity	NPD5210	Approved
0.5612	Remote Similarity	NPD6081	Approved
0.561	Remote Similarity	NPD5167	Approved
0.5607	Remote Similarity	NPD3618	Phase 1
0.5603	Remote Similarity	NPD7632	Discontinued

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