NPASS Compound

Structure

CID223988 OpenBabel06191716022D 33 35 0 0 0 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -3.4641 -2.0000 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 1.7321 -0.0000 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 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.8660 -0.5000 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 -2.5981 -0.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 28 2 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 33 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.22
Volume:	484.761
LogP:	7.237
LogD:	4.08
LogS:	-2.71
# Rotatable Bonds:	7
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	3.188
Fsp3:	0.321
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.863
MDCK Permeability:	1.6887997844605707e-05
Pgp-inhibitor:	0.648
Pgp-substrate:	0.774
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.415

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.5300521850586%
Volume Distribution (VD):	0.947
Pgp-substrate:	7.963569641113281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.553
CYP1A2-substrate:	0.193
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.542
CYP2D6-substrate:	0.32
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	5.349
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.739
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.318
Skin Sensitization:	0.925
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.294
Respiratory Toxicity:	0.216

Download Data

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

Natural Product: NPC223988

Natural Product ID:	NPC223988
*Common Name:**	Cochinchinone A
IUPAC Name:	4-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3,7-trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	Cochinchinone A
Standard InCHIKey:	ZHJQVNDLFGICFY-VCHYOVAHSA-N
Standard InCHI:	InChI=1S/C28H32O5/c1-16(2)7-6-8-18(5)10-13-21-25(30)20(12-9-17(3)4)26(31)24-27(32)22-15-19(29)11-14-23(22)33-28(21)24/h7,9-11,14-15,29-31H,6,8,12-13H2,1-5H3/b18-10+
SMILES:	CC(=CCC/C(=C/Cc1c(c(CC=C(C)C)c(c2c(=O)c3cc(ccc3oc12)O)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782241
PubChem CID:	11633740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15182859]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[16310231]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[16651783]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428375]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	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
ED50	1
IC50	4
Ki	2

Activity Type	# Activity
Cell Line	2
Individual Protein	3
PROTEIN FAMILY	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[567227]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[567227]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5200.0	nM	PMID[567228]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	3100.0	nM	PMID[567228]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[567227]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	Ki	=	13400.0	nM	PMID[567228]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	=	17400.0	nM	PMID[567228]

☑ 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 NPC223988 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	430
0.1-0.2	1751
0.2-0.3	4359
0.3-0.4	11083
0.4-0.5	7017
0.5-0.6	3747
0.6-0.7	5399
0.7-0.8	4480
0.8-0.85	2067
0.85-0.9	1780
0.9-0.95	561
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC37135
0.993	High Similarity	NPC186397
0.986	High Similarity	NPC266499
0.9655	High Similarity	NPC120105
0.9655	High Similarity	NPC227122
0.9655	High Similarity	NPC101957
0.9577	High Similarity	NPC159855
0.9577	High Similarity	NPC169479
0.9459	High Similarity	NPC95842
0.9459	High Similarity	NPC178964
0.9459	High Similarity	NPC280530
0.9441	High Similarity	NPC144499
0.9437	High Similarity	NPC69769
0.9396	High Similarity	NPC113906
0.9388	High Similarity	NPC37348
0.9384	High Similarity	NPC39195
0.9384	High Similarity	NPC145467
0.9379	High Similarity	NPC24136
0.9379	High Similarity	NPC187282
0.9379	High Similarity	NPC290133
0.9375	High Similarity	NPC106985
0.9375	High Similarity	NPC166138
0.9375	High Similarity	NPC18585
0.9342	High Similarity	NPC3629
0.9338	High Similarity	NPC172770
0.9338	High Similarity	NPC185258
0.9333	High Similarity	NPC191146
0.9333	High Similarity	NPC138243
0.9333	High Similarity	NPC68093
0.932	High Similarity	NPC10027
0.932	High Similarity	NPC65775
0.932	High Similarity	NPC269420
0.9315	High Similarity	NPC308200
0.931	High Similarity	NPC234629
0.931	High Similarity	NPC236766
0.931	High Similarity	NPC311741
0.931	High Similarity	NPC197252
0.9301	High Similarity	NPC270883
0.9301	High Similarity	NPC172986
0.9301	High Similarity	NPC145673
0.9301	High Similarity	NPC261227
0.9296	High Similarity	NPC18457
0.9276	High Similarity	NPC471976
0.9272	High Similarity	NPC36852
0.9272	High Similarity	NPC196448
0.9272	High Similarity	NPC262286
0.9272	High Similarity	NPC476981
0.9272	High Similarity	NPC236796
0.9272	High Similarity	NPC78225
0.9272	High Similarity	NPC79053
0.9267	High Similarity	NPC55662
0.9267	High Similarity	NPC166054
0.9262	High Similarity	NPC142527
0.9262	High Similarity	NPC474843
0.9262	High Similarity	NPC249570
0.9257	High Similarity	NPC230713
0.9257	High Similarity	NPC472633
0.9257	High Similarity	NPC78335
0.9247	High Similarity	NPC472629
0.9247	High Similarity	NPC196114
0.9247	High Similarity	NPC299011
0.9247	High Similarity	NPC477955
0.9241	High Similarity	NPC24821
0.9241	High Similarity	NPC75049
0.9241	High Similarity	NPC221432
0.9241	High Similarity	NPC175504
0.9241	High Similarity	NPC185276
0.9241	High Similarity	NPC164980
0.9241	High Similarity	NPC169591
0.9241	High Similarity	NPC39329
0.9241	High Similarity	NPC293053
0.9241	High Similarity	NPC149026
0.9241	High Similarity	NPC310130
0.9241	High Similarity	NPC38219
0.9241	High Similarity	NPC143896
0.9241	High Similarity	NPC257097
0.9241	High Similarity	NPC150408
0.9241	High Similarity	NPC219915
0.9241	High Similarity	NPC9117
0.9241	High Similarity	NPC91560
0.9241	High Similarity	NPC212932
0.9241	High Similarity	NPC190637
0.9241	High Similarity	NPC68104
0.9236	High Similarity	NPC147688
0.9236	High Similarity	NPC205006
0.9236	High Similarity	NPC110969
0.9236	High Similarity	NPC156590
0.9236	High Similarity	NPC118840
0.9236	High Similarity	NPC3188
0.9236	High Similarity	NPC64908
0.9231	High Similarity	NPC96565
0.9231	High Similarity	NPC216978
0.9231	High Similarity	NPC55018
0.9231	High Similarity	NPC303633
0.9231	High Similarity	NPC220062
0.9231	High Similarity	NPC301217
0.9216	High Similarity	NPC472275
0.9216	High Similarity	NPC167678
0.9216	High Similarity	NPC474187
0.9216	High Similarity	NPC29876
0.9205	High Similarity	NPC142339
0.92	High Similarity	NPC33051
0.92	High Similarity	NPC472915
0.92	High Similarity	NPC227337
0.92	High Similarity	NPC273462
0.92	High Similarity	NPC49402
0.92	High Similarity	NPC476631
0.92	High Similarity	NPC472462
0.92	High Similarity	NPC70433
0.92	High Similarity	NPC135522
0.9195	High Similarity	NPC170169
0.9195	High Similarity	NPC117579
0.9195	High Similarity	NPC149614
0.9189	High Similarity	NPC317492
0.9189	High Similarity	NPC471114
0.9189	High Similarity	NPC178202
0.9178	High Similarity	NPC235217
0.9178	High Similarity	NPC271288
0.9178	High Similarity	NPC326500
0.9178	High Similarity	NPC303185
0.9178	High Similarity	NPC473013
0.9178	High Similarity	NPC470890
0.9178	High Similarity	NPC87486
0.9178	High Similarity	NPC184649
0.9178	High Similarity	NPC216538
0.9178	High Similarity	NPC124780
0.9178	High Similarity	NPC473015
0.9178	High Similarity	NPC311144
0.9178	High Similarity	NPC473014
0.9178	High Similarity	NPC273538
0.9178	High Similarity	NPC209040
0.9172	High Similarity	NPC37496
0.9172	High Similarity	NPC228504
0.9172	High Similarity	NPC78
0.9172	High Similarity	NPC40833
0.9172	High Similarity	NPC306829
0.9172	High Similarity	NPC11561
0.9172	High Similarity	NPC76372
0.9172	High Similarity	NPC166934
0.9172	High Similarity	NPC107572
0.9172	High Similarity	NPC148757
0.9172	High Similarity	NPC76338
0.9172	High Similarity	NPC10937
0.9172	High Similarity	NPC125855
0.9172	High Similarity	NPC226636
0.9172	High Similarity	NPC167624
0.9172	High Similarity	NPC1089
0.9172	High Similarity	NPC200694
0.9172	High Similarity	NPC194432
0.9172	High Similarity	NPC473042
0.9172	High Similarity	NPC220998
0.9172	High Similarity	NPC73028
0.9172	High Similarity	NPC32739
0.9172	High Similarity	NPC328164
0.9172	High Similarity	NPC265040
0.9172	High Similarity	NPC227579
0.9172	High Similarity	NPC166482
0.9172	High Similarity	NPC324436
0.9172	High Similarity	NPC177354
0.9172	High Similarity	NPC223500
0.9172	High Similarity	NPC296917
0.9172	High Similarity	NPC64915
0.9172	High Similarity	NPC66515
0.9172	High Similarity	NPC324134
0.9172	High Similarity	NPC182852
0.9172	High Similarity	NPC161506
0.9167	High Similarity	NPC305355
0.9167	High Similarity	NPC235239
0.9167	High Similarity	NPC475680
0.9167	High Similarity	NPC241100
0.9167	High Similarity	NPC159275
0.9161	High Similarity	NPC201395
0.9156	High Similarity	NPC472448
0.9156	High Similarity	NPC329760
0.9156	High Similarity	NPC83922
0.915	High Similarity	NPC320359
0.915	High Similarity	NPC119224
0.915	High Similarity	NPC476980
0.915	High Similarity	NPC474287
0.915	High Similarity	NPC475886
0.915	High Similarity	NPC204290
0.915	High Similarity	NPC45146
0.915	High Similarity	NPC235018
0.9145	High Similarity	NPC476630
0.9145	High Similarity	NPC217677
0.9145	High Similarity	NPC181960
0.9145	High Similarity	NPC165977
0.9145	High Similarity	NPC218871
0.9139	High Similarity	NPC152951
0.9139	High Similarity	NPC57674
0.9139	High Similarity	NPC226025
0.9139	High Similarity	NPC472909
0.9139	High Similarity	NPC37392
0.9139	High Similarity	NPC213936
0.9139	High Similarity	NPC297531
0.9139	High Similarity	NPC168247
0.9139	High Similarity	NPC275575
0.9139	High Similarity	NPC117992
0.9139	High Similarity	NPC230149
0.9133	High Similarity	NPC45934

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 NPC223988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	975
0.2-0.3	1586
0.3-0.4	2654
0.4-0.5	1909
0.5-0.6	1077
0.6-0.7	367
0.7-0.8	124
0.8-0.85	48
0.85-0.9	19
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD4378	Clinical (unspecified phase)
0.9073	High Similarity	NPD2393	Clinical (unspecified phase)
0.8947	High Similarity	NPD2801	Approved
0.8947	High Similarity	NPD7819	Suspended
0.8919	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD1549	Phase 2
0.8828	High Similarity	NPD1552	Clinical (unspecified phase)
0.8828	High Similarity	NPD1550	Clinical (unspecified phase)
0.8774	High Similarity	NPD7075	Discontinued
0.8766	High Similarity	NPD8443	Clinical (unspecified phase)
0.8758	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD4380	Phase 2
0.8725	High Similarity	NPD1511	Approved
0.8701	High Similarity	NPD7096	Clinical (unspecified phase)
0.8693	High Similarity	NPD7411	Suspended
0.869	High Similarity	NPD1510	Phase 2
0.8671	High Similarity	NPD1240	Approved
0.8662	High Similarity	NPD5494	Approved
0.863	High Similarity	NPD2796	Approved
0.863	High Similarity	NPD2935	Discontinued
0.8609	High Similarity	NPD1512	Approved
0.8552	High Similarity	NPD1607	Approved
0.8491	Intermediate Similarity	NPD6959	Discontinued
0.8471	Intermediate Similarity	NPD3882	Suspended
0.8456	Intermediate Similarity	NPD2800	Approved
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3749	Approved
0.8293	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7473	Discontinued
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD3750	Approved
0.8242	Intermediate Similarity	NPD7074	Phase 3
0.8239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6799	Approved
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6232	Discontinued
0.8205	Intermediate Similarity	NPD3226	Approved
0.82	Intermediate Similarity	NPD2346	Discontinued
0.8188	Intermediate Similarity	NPD2799	Discontinued
0.8188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD2533	Approved
0.8182	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD5402	Approved
0.8151	Intermediate Similarity	NPD2313	Discontinued
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8133	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD6099	Approved
0.8133	Intermediate Similarity	NPD6100	Approved
0.8095	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1243	Approved
0.8079	Intermediate Similarity	NPD2344	Approved
0.8077	Intermediate Similarity	NPD920	Approved
0.8072	Intermediate Similarity	NPD7286	Phase 2
0.8054	Intermediate Similarity	NPD6651	Approved
0.8041	Intermediate Similarity	NPD943	Approved
0.8039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8037	Intermediate Similarity	NPD1247	Approved
0.8036	Intermediate Similarity	NPD7251	Discontinued
0.8027	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7976	Intermediate Similarity	NPD5953	Discontinued
0.7976	Intermediate Similarity	NPD6797	Phase 2
0.7949	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3748	Approved
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.7885	Intermediate Similarity	NPD7390	Discontinued
0.7871	Intermediate Similarity	NPD2309	Approved
0.7829	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1203	Approved
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5403	Approved
0.7725	Intermediate Similarity	NPD3926	Phase 2
0.7718	Intermediate Similarity	NPD4625	Phase 3
0.7716	Intermediate Similarity	NPD6844	Discontinued
0.7697	Intermediate Similarity	NPD919	Approved
0.7665	Intermediate Similarity	NPD5710	Approved
0.7665	Intermediate Similarity	NPD5711	Approved
0.7655	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6832	Phase 2
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7651	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2798	Approved
0.7632	Intermediate Similarity	NPD447	Suspended
0.7624	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5401	Approved
0.7603	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7568	Intermediate Similarity	NPD1470	Approved
0.756	Intermediate Similarity	NPD7229	Phase 3
0.755	Intermediate Similarity	NPD3268	Approved
0.7542	Intermediate Similarity	NPD4363	Phase 3
0.7542	Intermediate Similarity	NPD4360	Phase 2
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4308	Phase 3
0.7483	Intermediate Similarity	NPD1608	Approved
0.7467	Intermediate Similarity	NPD2861	Phase 2
0.7451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1613	Approved
0.745	Intermediate Similarity	NPD2797	Approved
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7434	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD6780	Approved
0.7432	Intermediate Similarity	NPD6781	Approved
0.7432	Intermediate Similarity	NPD4749	Approved
0.7432	Intermediate Similarity	NPD6777	Approved
0.7432	Intermediate Similarity	NPD6782	Approved
0.7432	Intermediate Similarity	NPD6776	Approved
0.7432	Intermediate Similarity	NPD6778	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7415	Intermediate Similarity	NPD1201	Approved
0.7413	Intermediate Similarity	NPD6671	Approved
0.7405	Intermediate Similarity	NPD7696	Phase 3
0.7405	Intermediate Similarity	NPD7697	Approved
0.7405	Intermediate Similarity	NPD7435	Discontinued
0.7405	Intermediate Similarity	NPD7698	Approved
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1471	Phase 3
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7366	Intermediate Similarity	NPD7871	Phase 2
0.7366	Intermediate Similarity	NPD7870	Phase 2
0.7363	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.732	Intermediate Similarity	NPD3764	Approved
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4287	Approved
0.7317	Intermediate Similarity	NPD7458	Discontinued
0.7308	Intermediate Similarity	NPD4361	Phase 2
0.7308	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4288	Approved
0.7305	Intermediate Similarity	NPD2296	Approved
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7299	Intermediate Similarity	NPD1729	Discontinued
0.7296	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD5124	Phase 1
0.729	Intermediate Similarity	NPD1933	Approved
0.729	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7584	Approved
0.7279	Intermediate Similarity	NPD17	Approved
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3225	Approved
0.7258	Intermediate Similarity	NPD6823	Phase 2
0.7249	Intermediate Similarity	NPD7701	Phase 2
0.7248	Intermediate Similarity	NPD3972	Approved
0.7248	Intermediate Similarity	NPD1481	Phase 2
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5760	Phase 2
0.7246	Intermediate Similarity	NPD5761	Phase 2
0.7226	Intermediate Similarity	NPD4307	Phase 2
0.7225	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7783	Phase 2
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD3267	Approved
0.7216	Intermediate Similarity	NPD6104	Discontinued
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7184	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1535	Discovery
0.7173	Intermediate Similarity	NPD7874	Approved
0.7173	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6585	Discontinued
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7152	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD7003	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