NPASS Compound

Structure

CID329048 OpenBabel06191716202D 38 39 0 0 1 0 0 0 0 0999 V2000 5.0817 -2.8179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0162 -3.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0951 -0.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8872 -1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6071 -7.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0138 -4.5313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2052 -6.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.7294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6998 -4.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7216 -4.5121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3689 -3.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4344 -3.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1254 -2.4021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 -5.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 -8.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4731 -4.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4731 -7.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6561 -6.7539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4126 -3.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3470 -4.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0683 -5.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 -6.4449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6071 -6.4449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2052 -7.9449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1473 -2.1942 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.6561 -5.1359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7052 -6.0789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8383 -1.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4731 -6.9449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6071 -5.4449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2052 -6.9449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0683 -5.9449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0712 -8.4449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7052 -6.0789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2052 -5.2128 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.5074 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -2.9373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6969 0.4744 0.0000 Na 0 3 0 0 0 15 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 8 37 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 20 26 2 0 0 0 0 21 26 1 0 0 0 0 21 32 2 0 0 0 0 22 29 1 1 0 0 0 22 31 1 0 0 0 0 23 29 1 6 0 0 0 23 30 1 0 0 0 0 24 31 1 6 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 37 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 29 5 1 1 0 0 0 30 6 1 6 0 0 0 31 7 1 6 0 0 0 M CHG 2 35 -1 38 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	513.32
Volume:	554.667
LogP:	2.104
LogD:	0.499
LogS:	-4.102
# Rotatable Bonds:	7
TPSA:	106.89
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	5.339
Fsp3:	0.677
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.959
MDCK Permeability:	3.4193431929452345e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.622
Plasma Protein Binding (PPB):	92.00972747802734%
Volume Distribution (VD):	0.503
Pgp-substrate:	7.859976768493652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.456
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.593

ADMET: Excretion

Clearance (CL):	1.877
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.434
Human Hepatotoxicity (H-HT):	0.618
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.9
Carcinogencity:	0.071
Eye Corrosion:	0.003
Eye Irritation:	0.012
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: NPC329048

Natural Product ID:	NPC329048
*Common Name:**	Globostellatic Acid D
IUPAC Name:	sodium;(3Z,3aS,5aR,6R,7R,9aR,9bS)-7-hydroxy-3-[(3E,5E,7E)-10-hydroxy-9-methoxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms:	Globostellatic Acid D
Standard InCHIKey:	CERBHPPRQFHGMC-PULODHPASA-M
Standard InCHI:	InChI=1S/C31H46O6.Na/c1-19(12-13-25(37-8)28(3,4)36)10-9-11-20(2)26-21(32)18-23-29(5)17-15-24(33)31(7,27(34)35)22(29)14-16-30(23,26)6;/h9-13,22-25,33,36H,14-18H2,1-8H3,(H,34,35);/q;+1/p-1/b11-9+,13-12+,19-10+,26-20+;/t22-,23+,24-,25?,29+,30+,31-;/m1./s1
SMILES:	COC(C(O)(C)C)/C=C/C(=C/C=C/C(=C/1C(=O)C[C@@H]2[C@]1(C)CC[C@@H]1[C@]2(C)CC[C@H]([C@]1(C)C(=O)[O-])O)/C)/C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465821
PubChem CID:	23682811
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
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO10924	Stelletta globostellata	Species	Ancorinidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[457111]

☑ 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 NPC329048 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	194
0.1-0.2	961
0.2-0.3	3308
0.3-0.4	6562
0.4-0.5	13807
0.5-0.6	7576
0.6-0.7	7100
0.7-0.8	2990
0.8-0.85	152
0.85-0.9	29
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC330011
0.98	High Similarity	NPC475065
0.97	High Similarity	NPC318363
0.97	High Similarity	NPC475418
0.97	High Similarity	NPC473482
0.9495	High Similarity	NPC475050
0.9406	High Similarity	NPC473284
0.92	High Similarity	NPC114540
0.92	High Similarity	NPC32577
0.92	High Similarity	NPC155332
0.9109	High Similarity	NPC473283
0.9109	High Similarity	NPC329345
0.9109	High Similarity	NPC475526
0.91	High Similarity	NPC282524
0.9091	High Similarity	NPC57079
0.9091	High Similarity	NPC108368
0.9082	High Similarity	NPC471153
0.899	High Similarity	NPC474938
0.899	High Similarity	NPC474785
0.898	High Similarity	NPC88310
0.8922	High Similarity	NPC72151
0.8911	High Similarity	NPC115899
0.8824	High Similarity	NPC320447
0.8812	High Similarity	NPC266955
0.8807	High Similarity	NPC167606
0.8807	High Similarity	NPC470492
0.8807	High Similarity	NPC286528
0.8807	High Similarity	NPC20302
0.8807	High Similarity	NPC140055
0.88	High Similarity	NPC2049
0.88	High Similarity	NPC110937
0.8796	High Similarity	NPC67259
0.8796	High Similarity	NPC147912
0.875	High Similarity	NPC266570
0.8727	High Similarity	NPC709
0.8727	High Similarity	NPC50774
0.87	High Similarity	NPC250757
0.87	High Similarity	NPC301534
0.8692	High Similarity	NPC474315
0.8687	High Similarity	NPC474690
0.8649	High Similarity	NPC264954
0.8636	High Similarity	NPC183580
0.8636	High Similarity	NPC312824
0.8636	High Similarity	NPC470493
0.8627	High Similarity	NPC35751
0.86	High Similarity	NPC180950
0.8571	High Similarity	NPC474370
0.8559	High Similarity	NPC473828
0.8559	High Similarity	NPC473617
0.8532	High Similarity	NPC122056
0.8529	High Similarity	NPC316598
0.8505	High Similarity	NPC173905
0.8505	High Similarity	NPC5475
0.8505	High Similarity	NPC472216
0.8505	High Similarity	NPC284828
0.85	High Similarity	NPC299100
0.85	High Similarity	NPC471078
0.85	High Similarity	NPC473280
0.85	High Similarity	NPC473435
0.85	High Similarity	NPC473431
0.8496	Intermediate Similarity	NPC67569
0.8491	Intermediate Similarity	NPC187435
0.8491	Intermediate Similarity	NPC67321
0.8468	Intermediate Similarity	NPC470959
0.8468	Intermediate Similarity	NPC476965
0.8455	Intermediate Similarity	NPC475163
0.844	Intermediate Similarity	NPC191620
0.8431	Intermediate Similarity	NPC73911
0.8431	Intermediate Similarity	NPC253826
0.8426	Intermediate Similarity	NPC29133
0.8421	Intermediate Similarity	NPC88326
0.8421	Intermediate Similarity	NPC153700
0.8421	Intermediate Similarity	NPC470265
0.8421	Intermediate Similarity	NPC23786
0.8416	Intermediate Similarity	NPC209355
0.8411	Intermediate Similarity	NPC306265
0.8411	Intermediate Similarity	NPC220155
0.8396	Intermediate Similarity	NPC189863
0.8396	Intermediate Similarity	NPC477125
0.8393	Intermediate Similarity	NPC186525
0.8384	Intermediate Similarity	NPC161638
0.8381	Intermediate Similarity	NPC112009
0.8378	Intermediate Similarity	NPC64318
0.8378	Intermediate Similarity	NPC270929
0.8367	Intermediate Similarity	NPC292491
0.8367	Intermediate Similarity	NPC310752
0.8365	Intermediate Similarity	NPC303559
0.835	Intermediate Similarity	NPC278386
0.835	Intermediate Similarity	NPC124512
0.835	Intermediate Similarity	NPC159763
0.8349	Intermediate Similarity	NPC470961
0.8348	Intermediate Similarity	NPC469789
0.8348	Intermediate Similarity	NPC11895
0.8333	Intermediate Similarity	NPC151725
0.8333	Intermediate Similarity	NPC242848
0.8333	Intermediate Similarity	NPC10064
0.8333	Intermediate Similarity	NPC106425
0.8333	Intermediate Similarity	NPC122324
0.8333	Intermediate Similarity	NPC170221
0.8319	Intermediate Similarity	NPC473274
0.8318	Intermediate Similarity	NPC255387
0.8318	Intermediate Similarity	NPC131665
0.8302	Intermediate Similarity	NPC473175
0.8288	Intermediate Similarity	NPC284915
0.8286	Intermediate Similarity	NPC473163
0.8286	Intermediate Similarity	NPC476081
0.8276	Intermediate Similarity	NPC470494
0.8276	Intermediate Similarity	NPC8374
0.8276	Intermediate Similarity	NPC81736
0.8276	Intermediate Similarity	NPC172154
0.8276	Intermediate Similarity	NPC3381
0.8276	Intermediate Similarity	NPC8369
0.8273	Intermediate Similarity	NPC69291
0.8273	Intermediate Similarity	NPC470063
0.8269	Intermediate Similarity	NPC476299
0.8269	Intermediate Similarity	NPC117685
0.8269	Intermediate Similarity	NPC474012
0.8265	Intermediate Similarity	NPC141292
0.8261	Intermediate Similarity	NPC170538
0.8257	Intermediate Similarity	NPC6206
0.8246	Intermediate Similarity	NPC476962
0.8246	Intermediate Similarity	NPC476961
0.8241	Intermediate Similarity	NPC472825
0.823	Intermediate Similarity	NPC257457
0.823	Intermediate Similarity	NPC311554
0.823	Intermediate Similarity	NPC329736
0.8224	Intermediate Similarity	NPC34768
0.8224	Intermediate Similarity	NPC173172
0.8224	Intermediate Similarity	NPC475414
0.8218	Intermediate Similarity	NPC162615
0.8218	Intermediate Similarity	NPC139692
0.8218	Intermediate Similarity	NPC152778
0.8218	Intermediate Similarity	NPC205034
0.8208	Intermediate Similarity	NPC120321
0.8208	Intermediate Similarity	NPC324001
0.8208	Intermediate Similarity	NPC23584
0.8208	Intermediate Similarity	NPC180204
0.8205	Intermediate Similarity	NPC293112
0.82	Intermediate Similarity	NPC475965
0.82	Intermediate Similarity	NPC474842
0.819	Intermediate Similarity	NPC194028
0.819	Intermediate Similarity	NPC476897
0.819	Intermediate Similarity	NPC168319
0.819	Intermediate Similarity	NPC473174
0.8182	Intermediate Similarity	NPC324683
0.8174	Intermediate Similarity	NPC473256
0.8174	Intermediate Similarity	NPC470878
0.8174	Intermediate Similarity	NPC46570
0.8158	Intermediate Similarity	NPC305260
0.8158	Intermediate Similarity	NPC473270
0.8158	Intermediate Similarity	NPC270850
0.8158	Intermediate Similarity	NPC61520
0.8155	Intermediate Similarity	NPC16967
0.8155	Intermediate Similarity	NPC473153
0.8148	Intermediate Similarity	NPC263729
0.8148	Intermediate Similarity	NPC475176
0.8148	Intermediate Similarity	NPC179380
0.8148	Intermediate Similarity	NPC91034
0.8148	Intermediate Similarity	NPC475294
0.8142	Intermediate Similarity	NPC243065
0.8142	Intermediate Similarity	NPC473656
0.8142	Intermediate Similarity	NPC476959
0.8137	Intermediate Similarity	NPC38830
0.8137	Intermediate Similarity	NPC191521
0.8131	Intermediate Similarity	NPC472868
0.8119	Intermediate Similarity	NPC473167
0.8119	Intermediate Similarity	NPC473986
0.8119	Intermediate Similarity	NPC303697
0.8119	Intermediate Similarity	NPC474018
0.8113	Intermediate Similarity	NPC11956
0.8113	Intermediate Similarity	NPC476890
0.8108	Intermediate Similarity	NPC476801
0.8108	Intermediate Similarity	NPC475970
0.8108	Intermediate Similarity	NPC269530
0.8103	Intermediate Similarity	NPC269642
0.8103	Intermediate Similarity	NPC107493
0.81	Intermediate Similarity	NPC36668
0.81	Intermediate Similarity	NPC118011
0.8095	Intermediate Similarity	NPC38855
0.8095	Intermediate Similarity	NPC201406
0.8095	Intermediate Similarity	NPC473510
0.8095	Intermediate Similarity	NPC477521
0.8091	Intermediate Similarity	NPC472215
0.8091	Intermediate Similarity	NPC472214
0.8091	Intermediate Similarity	NPC179642
0.8091	Intermediate Similarity	NPC16270
0.8091	Intermediate Similarity	NPC37116
0.8087	Intermediate Similarity	NPC184555
0.8077	Intermediate Similarity	NPC53844
0.8077	Intermediate Similarity	NPC210337
0.8077	Intermediate Similarity	NPC108078
0.8073	Intermediate Similarity	NPC151393
0.8073	Intermediate Similarity	NPC472219
0.8073	Intermediate Similarity	NPC472218
0.8073	Intermediate Similarity	NPC472217
0.807	Intermediate Similarity	NPC146786
0.807	Intermediate Similarity	NPC284707
0.8058	Intermediate Similarity	NPC469329
0.8058	Intermediate Similarity	NPC30677
0.8058	Intermediate Similarity	NPC37787

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 NPC329048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1128
0.2-0.3	3253
0.3-0.4	2845
0.4-0.5	1128
0.5-0.6	300
0.6-0.7	210
0.7-0.8	121
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD7115	Discovery
0.835	Intermediate Similarity	NPD4225	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.7925	Intermediate Similarity	NPD7640	Approved
0.7925	Intermediate Similarity	NPD7639	Approved
0.7788	Intermediate Similarity	NPD8297	Approved
0.7748	Intermediate Similarity	NPD6881	Approved
0.7748	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD6675	Approved
0.7727	Intermediate Similarity	NPD7128	Approved
0.7727	Intermediate Similarity	NPD6402	Approved
0.7727	Intermediate Similarity	NPD5739	Approved
0.767	Intermediate Similarity	NPD5785	Approved
0.7658	Intermediate Similarity	NPD5697	Approved
0.7627	Intermediate Similarity	NPD6319	Approved
0.7624	Intermediate Similarity	NPD3618	Phase 1
0.7611	Intermediate Similarity	NPD6883	Approved
0.7611	Intermediate Similarity	NPD7290	Approved
0.7611	Intermediate Similarity	NPD7102	Approved
0.7596	Intermediate Similarity	NPD6079	Approved
0.7596	Intermediate Similarity	NPD7637	Suspended
0.7596	Intermediate Similarity	NPD7515	Phase 2
0.7589	Intermediate Similarity	NPD7320	Approved
0.7573	Intermediate Similarity	NPD5328	Approved
0.757	Intermediate Similarity	NPD6083	Phase 2
0.757	Intermediate Similarity	NPD6084	Phase 2
0.7565	Intermediate Similarity	NPD4632	Approved
0.7561	Intermediate Similarity	NPD7319	Approved
0.7544	Intermediate Similarity	NPD6617	Approved
0.7544	Intermediate Similarity	NPD6847	Approved
0.7544	Intermediate Similarity	NPD6650	Approved
0.7544	Intermediate Similarity	NPD6869	Approved
0.7544	Intermediate Similarity	NPD6649	Approved
0.7544	Intermediate Similarity	NPD8130	Phase 1
0.7524	Intermediate Similarity	NPD6399	Phase 3
0.7522	Intermediate Similarity	NPD6372	Approved
0.7522	Intermediate Similarity	NPD6373	Approved
0.7522	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6013	Approved
0.7522	Intermediate Similarity	NPD6014	Approved
0.7522	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.7478	Intermediate Similarity	NPD6882	Approved
0.7459	Intermediate Similarity	NPD7507	Approved
0.7456	Intermediate Similarity	NPD4634	Approved
0.7455	Intermediate Similarity	NPD5211	Phase 2
0.7453	Intermediate Similarity	NPD7748	Approved
0.7434	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD6011	Approved
0.7434	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5285	Approved
0.7431	Intermediate Similarity	NPD5286	Approved
0.7431	Intermediate Similarity	NPD4696	Approved
0.7429	Intermediate Similarity	NPD6411	Approved
0.7426	Intermediate Similarity	NPD4786	Approved
0.7407	Intermediate Similarity	NPD4755	Approved
0.74	Intermediate Similarity	NPD3667	Approved
0.7377	Intermediate Similarity	NPD7492	Approved
0.7358	Intermediate Similarity	NPD5778	Approved
0.7358	Intermediate Similarity	NPD5779	Approved
0.7358	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD6054	Approved
0.7321	Intermediate Similarity	NPD5141	Approved
0.7317	Intermediate Similarity	NPD6616	Approved
0.7315	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5221	Approved
0.7315	Intermediate Similarity	NPD5222	Approved
0.7297	Intermediate Similarity	NPD5224	Approved
0.7297	Intermediate Similarity	NPD7632	Discontinued
0.7297	Intermediate Similarity	NPD5225	Approved
0.7297	Intermediate Similarity	NPD5226	Approved
0.7297	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD7146	Approved
0.7282	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6409	Approved
0.7282	Intermediate Similarity	NPD5330	Approved
0.7282	Intermediate Similarity	NPD7521	Approved
0.7282	Intermediate Similarity	NPD7334	Approved
0.7282	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD7503	Approved
0.7273	Intermediate Similarity	NPD4700	Approved
0.7264	Intermediate Similarity	NPD5281	Approved
0.7264	Intermediate Similarity	NPD5284	Approved
0.7258	Intermediate Similarity	NPD7078	Approved
0.7255	Intermediate Similarity	NPD3666	Approved
0.7255	Intermediate Similarity	NPD3133	Approved
0.7255	Intermediate Similarity	NPD3665	Phase 1
0.7248	Intermediate Similarity	NPD7902	Approved
0.7248	Intermediate Similarity	NPD5173	Approved
0.7241	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4753	Phase 2
0.7238	Intermediate Similarity	NPD6101	Approved
0.7238	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5174	Approved
0.7232	Intermediate Similarity	NPD5175	Approved
0.7228	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6009	Approved
0.7222	Intermediate Similarity	NPD5695	Phase 3
0.7213	Intermediate Similarity	NPD6370	Approved
0.7207	Intermediate Similarity	NPD5223	Approved
0.72	Intermediate Similarity	NPD7736	Approved
0.7193	Intermediate Similarity	NPD6412	Phase 2
0.719	Intermediate Similarity	NPD6059	Approved
0.7184	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1694	Approved
0.7184	Intermediate Similarity	NPD5363	Approved
0.7182	Intermediate Similarity	NPD5696	Approved
0.7167	Intermediate Similarity	NPD7327	Approved
0.7167	Intermediate Similarity	NPD7328	Approved
0.7156	Intermediate Similarity	NPD4697	Phase 3
0.7155	Intermediate Similarity	NPD6371	Approved
0.7155	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8033	Approved
0.7131	Intermediate Similarity	NPD6016	Approved
0.7131	Intermediate Similarity	NPD6015	Approved
0.7129	Intermediate Similarity	NPD5369	Approved
0.712	Intermediate Similarity	NPD8293	Discontinued
0.7115	Intermediate Similarity	NPD5279	Phase 3
0.7107	Intermediate Similarity	NPD7516	Approved
0.7107	Intermediate Similarity	NPD7100	Approved
0.7107	Intermediate Similarity	NPD7101	Approved
0.7103	Intermediate Similarity	NPD5693	Phase 1
0.7073	Intermediate Similarity	NPD5988	Approved
0.7064	Intermediate Similarity	NPD5210	Approved
0.7064	Intermediate Similarity	NPD4629	Approved
0.7064	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4269	Approved
0.7059	Intermediate Similarity	NPD4270	Approved
0.7054	Intermediate Similarity	NPD5344	Discontinued
0.7049	Intermediate Similarity	NPD8377	Approved
0.7049	Intermediate Similarity	NPD8294	Approved
0.7048	Intermediate Similarity	NPD7524	Approved
0.7025	Intermediate Similarity	NPD6335	Approved
0.7016	Intermediate Similarity	NPD7604	Phase 2
0.7009	Intermediate Similarity	NPD6698	Approved
0.7009	Intermediate Similarity	NPD46	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD6868	Approved
0.6992	Remote Similarity	NPD8296	Approved
0.6992	Remote Similarity	NPD8513	Phase 3
0.6992	Remote Similarity	NPD8515	Approved
0.6992	Remote Similarity	NPD8517	Approved
0.6992	Remote Similarity	NPD8380	Approved
0.6992	Remote Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD8516	Approved
0.6992	Remote Similarity	NPD8379	Approved
0.6992	Remote Similarity	NPD8378	Approved
0.6992	Remote Similarity	NPD8335	Approved
0.6983	Remote Similarity	NPD4730	Approved
0.6983	Remote Similarity	NPD4729	Approved
0.6972	Remote Similarity	NPD7900	Approved
0.6972	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6933	Approved
0.6964	Remote Similarity	NPD6648	Approved
0.6957	Remote Similarity	NPD4767	Approved
0.6957	Remote Similarity	NPD4768	Approved
0.6957	Remote Similarity	NPD6008	Approved
0.6952	Remote Similarity	NPD5786	Approved
0.6944	Remote Similarity	NPD6050	Approved
0.6944	Remote Similarity	NPD7983	Approved
0.6944	Remote Similarity	NPD8035	Phase 2
0.6944	Remote Similarity	NPD8034	Phase 2
0.6944	Remote Similarity	NPD5694	Approved
0.6942	Remote Similarity	NPD6317	Approved
0.693	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD3668	Phase 3
0.6916	Remote Similarity	NPD6673	Approved
0.6916	Remote Similarity	NPD6904	Approved
0.6916	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6080	Approved
0.6905	Remote Similarity	NPD6336	Discontinued
0.6897	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4223	Phase 3
0.6893	Remote Similarity	NPD4221	Approved
0.6891	Remote Similarity	NPD6053	Discontinued
0.6887	Remote Similarity	NPD3573	Approved
0.6885	Remote Similarity	NPD6313	Approved
0.6885	Remote Similarity	NPD6314	Approved
0.688	Remote Similarity	NPD8328	Phase 3
0.6864	Remote Similarity	NPD5251	Approved
0.6864	Remote Similarity	NPD5250	Approved
0.6864	Remote Similarity	NPD5249	Phase 3
0.6864	Remote Similarity	NPD5248	Approved
0.6864	Remote Similarity	NPD5247	Approved
0.6863	Remote Similarity	NPD7525	Registered
0.6863	Remote Similarity	NPD4252	Approved
0.6857	Remote Similarity	NPD5329	Approved
0.6855	Remote Similarity	NPD6908	Approved
0.6855	Remote Similarity	NPD6909	Approved
0.6852	Remote Similarity	NPD5207	Approved
0.6852	Remote Similarity	NPD5692	Phase 3
0.6852	Remote Similarity	NPD7838	Discovery
0.6838	Remote Similarity	NPD5128	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