NPASS Compound

Structure

CID225597 OpenBabel06191716022D 23 27 0 0 1 0 0 0 0 0999 V2000 2.2831 0.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8523 -1.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4895 -1.8676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1855 -0.5824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4256 0.0916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4256 -1.7580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4011 -0.8333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6496 -0.8332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7170 -0.8332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6247 -0.3708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6247 -1.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2265 -0.3708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2265 -1.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7689 -0.7831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 -1.6666 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9016 0.2057 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9018 -1.8722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.5392 -2.3431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0941 1.0492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4263 -0.2583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1060 -0.0850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1060 -1.5814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 4 9 1 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 7 18 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 21 1 1 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 1 0 0 0 14 18 1 0 0 0 0 15 17 1 6 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.13
Volume:	304.208
LogP:	0.508
LogD:	0.912
LogS:	-2.36
# Rotatable Bonds:	1
TPSA:	71.39
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	5.528
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008
MDCK Permeability:	3.451506563578732e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.769
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.679
30% Bioavailability (F30%):	0.101

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.753
Plasma Protein Binding (PPB):	49.188720703125%
Volume Distribution (VD):	1.586
Pgp-substrate:	52.003353118896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.406
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.564
CYP3A4-substrate:	0.635

ADMET: Excretion

Clearance (CL):	5.415
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.423
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.37
Carcinogencity:	0.657
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC225597

Natural Product ID:	NPC225597
*Common Name:**	ZSTPNQLNQBRLQF-KTZSIVBYSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-6-Hydroxycrinamine
Standard InCHIKey:	ZSTPNQLNQBRLQF-KTZSIVBYSA-N
Standard InCHI:	InChI=1S/C17H19NO5/c1-21-9-2-3-17-11-6-13-12(22-8-23-13)5-10(11)16(20)18(7-15(17)19)14(17)4-9/h2-3,5-6,9,14-16,19-20H,4,7-8H2,1H3/t9-,14-,15+,16?,17+/m0/s1
SMILES:	CO[C@H]1C=C[C@@]23[C@H](C1)N(C[C@H]2O)C(c1c3cc2OCOc2c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512669
PubChem CID:	44559503
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae alkaloids

*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
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	DOI[10.1016/S0031-9422(00)00184-9]
NPO23263	Crinum yemense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270564]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[15587597]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23263	Crinum yemense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18113	Crinum bulbispermum	Species	Amaryllidaceae	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
Others	10

Activity Type	# Activity
Others	11

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	-11.2	%	PMID[529604]
NPT27	Others	Unspecified	Activity	=	110.1	%	PMID[529604]
NPT2	Others	Unspecified	Inhibition	=	-23.1	%	PMID[529604]
NPT27	Others	Unspecified	Activity	=	120.0	%	PMID[529604]
NPT2	Others	Unspecified	Inhibition	=	6.3	%	PMID[529604]
NPT27	Others	Unspecified	Activity	=	117.3	%	PMID[529604]
NPT2	Others	Unspecified	Inhibition	=	30.3	%	PMID[529604]
NPT27	Others	Unspecified	Activity	=	115.3	%	PMID[529604]
NPT2	Others	Unspecified	Inhibition	=	69.5	%	PMID[529604]
NPT27	Others	Unspecified	Activity	=	108.3	%	PMID[529604]
NPT2	Others	Unspecified	IC50	=	5400.0	nM	PMID[529604]

☑ 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 NPC225597 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	274
0.1-0.2	1256
0.2-0.3	4082
0.3-0.4	11837
0.4-0.5	7793
0.5-0.6	12799
0.6-0.7	3685
0.7-0.8	734
0.8-0.85	137
0.85-0.9	56
0.9-0.95	32
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470739
1.0	High Similarity	NPC477640
0.9936	High Similarity	NPC474475
0.9873	High Similarity	NPC82533
0.9873	High Similarity	NPC158148
0.9873	High Similarity	NPC58766
0.9873	High Similarity	NPC266176
0.9873	High Similarity	NPC290759
0.9873	High Similarity	NPC475686
0.9568	High Similarity	NPC474470
0.949	High Similarity	NPC97072
0.949	High Similarity	NPC215829
0.9451	High Similarity	NPC244554
0.9437	High Similarity	NPC100566
0.9437	High Similarity	NPC252960
0.9371	High Similarity	NPC218614
0.9317	High Similarity	NPC181653
0.9317	High Similarity	NPC190332
0.925	High Similarity	NPC320104
0.9236	High Similarity	NPC78733
0.9207	High Similarity	NPC2314
0.9202	High Similarity	NPC311991
0.9193	High Similarity	NPC247972
0.9136	High Similarity	NPC476002
0.9096	High Similarity	NPC237044
0.9085	High Similarity	NPC75958
0.9062	High Similarity	NPC92191
0.9062	High Similarity	NPC59028
0.9042	High Similarity	NPC474325
0.9036	High Similarity	NPC304675
0.8988	High Similarity	NPC474745
0.8938	High Similarity	NPC147091
0.8929	High Similarity	NPC15919
0.8889	High Similarity	NPC4304
0.8889	High Similarity	NPC9867
0.8848	High Similarity	NPC57812
0.8848	High Similarity	NPC474324
0.883	High Similarity	NPC474746
0.883	High Similarity	NPC475981
0.8817	High Similarity	NPC148693
0.8817	High Similarity	NPC118633
0.8817	High Similarity	NPC294790
0.881	High Similarity	NPC187678
0.8802	High Similarity	NPC65403
0.8795	High Similarity	NPC475845
0.8773	High Similarity	NPC205167
0.8773	High Similarity	NPC249274
0.8772	High Similarity	NPC248642
0.875	High Similarity	NPC148898
0.8743	High Similarity	NPC474708
0.8728	High Similarity	NPC230098
0.8721	High Similarity	NPC156576
0.8698	High Similarity	NPC49353
0.8655	High Similarity	NPC126284
0.8625	High Similarity	NPC274026
0.8623	High Similarity	NPC150879
0.8616	High Similarity	NPC475959
0.8547	High Similarity	NPC99179
0.8519	High Similarity	NPC223124
0.8519	High Similarity	NPC210148
0.8519	High Similarity	NPC233029
0.8503	High Similarity	NPC238530
0.8503	High Similarity	NPC232514
0.8503	High Similarity	NPC276944
0.8485	Intermediate Similarity	NPC111485
0.8476	Intermediate Similarity	NPC234392
0.8476	Intermediate Similarity	NPC31311
0.8448	Intermediate Similarity	NPC275132
0.8448	Intermediate Similarity	NPC233718
0.8443	Intermediate Similarity	NPC233650
0.8415	Intermediate Similarity	NPC138487
0.8415	Intermediate Similarity	NPC41178
0.8415	Intermediate Similarity	NPC216459
0.8409	Intermediate Similarity	NPC214116
0.8405	Intermediate Similarity	NPC82285
0.8405	Intermediate Similarity	NPC133011
0.8395	Intermediate Similarity	NPC223125
0.8393	Intermediate Similarity	NPC134858
0.8393	Intermediate Similarity	NPC231198
0.8382	Intermediate Similarity	NPC320223
0.8382	Intermediate Similarity	NPC114364
0.8364	Intermediate Similarity	NPC146288
0.8363	Intermediate Similarity	NPC57272
0.8343	Intermediate Similarity	NPC102760
0.8323	Intermediate Similarity	NPC165797
0.8313	Intermediate Similarity	NPC78359
0.8313	Intermediate Similarity	NPC65490
0.8313	Intermediate Similarity	NPC148014
0.8313	Intermediate Similarity	NPC40389
0.8313	Intermediate Similarity	NPC130926
0.8313	Intermediate Similarity	NPC315707
0.8313	Intermediate Similarity	NPC185838
0.8294	Intermediate Similarity	NPC247389
0.8294	Intermediate Similarity	NPC210918
0.8294	Intermediate Similarity	NPC210140
0.8284	Intermediate Similarity	NPC180306
0.8272	Intermediate Similarity	NPC476571
0.8272	Intermediate Similarity	NPC246587
0.8272	Intermediate Similarity	NPC428
0.8272	Intermediate Similarity	NPC135538
0.8272	Intermediate Similarity	NPC24233
0.8272	Intermediate Similarity	NPC147390
0.8266	Intermediate Similarity	NPC128560
0.8266	Intermediate Similarity	NPC199465
0.8266	Intermediate Similarity	NPC229166
0.8263	Intermediate Similarity	NPC477080
0.8253	Intermediate Similarity	NPC160931
0.8253	Intermediate Similarity	NPC37205
0.8246	Intermediate Similarity	NPC160570
0.8239	Intermediate Similarity	NPC476575
0.8235	Intermediate Similarity	NPC24264
0.8235	Intermediate Similarity	NPC219341
0.8235	Intermediate Similarity	NPC476432
0.8235	Intermediate Similarity	NPC124657
0.8225	Intermediate Similarity	NPC59567
0.821	Intermediate Similarity	NPC179825
0.821	Intermediate Similarity	NPC476151
0.821	Intermediate Similarity	NPC191376
0.821	Intermediate Similarity	NPC321505
0.8187	Intermediate Similarity	NPC298979
0.8187	Intermediate Similarity	NPC298186
0.8187	Intermediate Similarity	NPC301189
0.8176	Intermediate Similarity	NPC302527
0.8176	Intermediate Similarity	NPC169743
0.8176	Intermediate Similarity	NPC328750
0.8176	Intermediate Similarity	NPC225774
0.8176	Intermediate Similarity	NPC16805
0.8176	Intermediate Similarity	NPC474915
0.8176	Intermediate Similarity	NPC167546
0.8176	Intermediate Similarity	NPC188163
0.8176	Intermediate Similarity	NPC213206
0.8156	Intermediate Similarity	NPC141440
0.8155	Intermediate Similarity	NPC69360
0.8153	Intermediate Similarity	NPC7018
0.8144	Intermediate Similarity	NPC180756
0.8144	Intermediate Similarity	NPC323443
0.8132	Intermediate Similarity	NPC33256
0.8122	Intermediate Similarity	NPC117717
0.8114	Intermediate Similarity	NPC283999
0.8113	Intermediate Similarity	NPC314682
0.811	Intermediate Similarity	NPC103379
0.811	Intermediate Similarity	NPC477565
0.8107	Intermediate Similarity	NPC18402
0.8095	Intermediate Similarity	NPC129603
0.8095	Intermediate Similarity	NPC475326
0.8092	Intermediate Similarity	NPC329911
0.809	Intermediate Similarity	NPC135772
0.8084	Intermediate Similarity	NPC2413
0.8084	Intermediate Similarity	NPC278799
0.8084	Intermediate Similarity	NPC110416
0.8084	Intermediate Similarity	NPC5238
0.8084	Intermediate Similarity	NPC249797
0.8084	Intermediate Similarity	NPC469817
0.8084	Intermediate Similarity	NPC127674
0.8084	Intermediate Similarity	NPC184026
0.8084	Intermediate Similarity	NPC193949
0.8084	Intermediate Similarity	NPC172765
0.8084	Intermediate Similarity	NPC276588
0.8084	Intermediate Similarity	NPC207757
0.8084	Intermediate Similarity	NPC76079
0.8084	Intermediate Similarity	NPC295691
0.8084	Intermediate Similarity	NPC39701
0.8084	Intermediate Similarity	NPC93593
0.8084	Intermediate Similarity	NPC204828
0.8084	Intermediate Similarity	NPC189266
0.8084	Intermediate Similarity	NPC54379
0.807	Intermediate Similarity	NPC76116
0.8066	Intermediate Similarity	NPC63152
0.8061	Intermediate Similarity	NPC97221
0.8061	Intermediate Similarity	NPC220858
0.8061	Intermediate Similarity	NPC88249
0.8061	Intermediate Similarity	NPC151895
0.8061	Intermediate Similarity	NPC192768
0.8049	Intermediate Similarity	NPC59907
0.8049	Intermediate Similarity	NPC37144
0.8047	Intermediate Similarity	NPC106786
0.8034	Intermediate Similarity	NPC116284
0.8023	Intermediate Similarity	NPC13916
0.8023	Intermediate Similarity	NPC264850
0.8023	Intermediate Similarity	NPC267408
0.8012	Intermediate Similarity	NPC293871
0.8012	Intermediate Similarity	NPC124433
0.8011	Intermediate Similarity	NPC241704
0.8	Intermediate Similarity	NPC306902
0.8	Intermediate Similarity	NPC477559
0.8	Intermediate Similarity	NPC207824
0.8	Intermediate Similarity	NPC60538
0.8	Intermediate Similarity	NPC266753
0.8	Intermediate Similarity	NPC232924
0.8	Intermediate Similarity	NPC160298
0.7989	Intermediate Similarity	NPC474953
0.7988	Intermediate Similarity	NPC51957
0.7988	Intermediate Similarity	NPC106295
0.7988	Intermediate Similarity	NPC16107
0.7988	Intermediate Similarity	NPC210437
0.7988	Intermediate Similarity	NPC476144
0.7978	Intermediate Similarity	NPC477561
0.7978	Intermediate Similarity	NPC312918
0.7978	Intermediate Similarity	NPC476574
0.7978	Intermediate Similarity	NPC155442

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 NPC225597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	596
0.2-0.3	946
0.3-0.4	2270
0.4-0.5	2700
0.5-0.6	1712
0.6-0.7	617
0.7-0.8	125
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8343	Intermediate Similarity	NPD6071	Discontinued
0.8313	Intermediate Similarity	NPD2560	Approved
0.8313	Intermediate Similarity	NPD2563	Approved
0.8253	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD2970	Approved
0.8187	Intermediate Similarity	NPD2969	Approved
0.8176	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD2978	Approved
0.8144	Intermediate Similarity	NPD2977	Approved
0.8133	Intermediate Similarity	NPD4773	Phase 2
0.8133	Intermediate Similarity	NPD4772	Phase 2
0.8035	Intermediate Similarity	NPD2489	Approved
0.8035	Intermediate Similarity	NPD27	Approved
0.8033	Intermediate Similarity	NPD5582	Discontinued
0.8025	Intermediate Similarity	NPD5241	Discontinued
0.8023	Intermediate Similarity	NPD3051	Approved
0.8012	Intermediate Similarity	NPD4236	Phase 3
0.8012	Intermediate Similarity	NPD4237	Approved
0.7988	Intermediate Similarity	NPD4584	Approved
0.7946	Intermediate Similarity	NPD4420	Approved
0.7929	Intermediate Similarity	NPD5772	Approved
0.7929	Intermediate Similarity	NPD5773	Approved
0.7901	Intermediate Similarity	NPD7906	Approved
0.7872	Intermediate Similarity	NPD5006	Approved
0.7872	Intermediate Similarity	NPD5005	Approved
0.7866	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD4663	Approved
0.7829	Intermediate Similarity	NPD4481	Phase 3
0.7829	Intermediate Similarity	NPD2898	Approved
0.7805	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7313	Approved
0.7778	Intermediate Similarity	NPD7311	Approved
0.7778	Intermediate Similarity	NPD7310	Approved
0.7778	Intermediate Similarity	NPD4577	Approved
0.7778	Intermediate Similarity	NPD4578	Approved
0.7778	Intermediate Similarity	NPD7312	Approved
0.7735	Intermediate Similarity	NPD7309	Approved
0.7705	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7280	Phase 3
0.768	Intermediate Similarity	NPD7281	Phase 3
0.7657	Intermediate Similarity	NPD6107	Approved
0.7633	Intermediate Similarity	NPD4210	Discontinued
0.7588	Intermediate Similarity	NPD4017	Approved
0.7586	Intermediate Similarity	NPD7833	Phase 2
0.7586	Intermediate Similarity	NPD5604	Discontinued
0.7586	Intermediate Similarity	NPD7831	Phase 2
0.7586	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7296	Approved
0.7576	Intermediate Similarity	NPD3060	Approved
0.7574	Intermediate Similarity	NPD3640	Phase 3
0.7574	Intermediate Similarity	NPD3639	Approved
0.7574	Intermediate Similarity	NPD3641	Approved
0.756	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8053	Approved
0.7541	Intermediate Similarity	NPD8054	Approved
0.7514	Intermediate Similarity	NPD4010	Discontinued
0.75	Intermediate Similarity	NPD8156	Discontinued
0.7485	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6030	Approved
0.7471	Intermediate Similarity	NPD6031	Approved
0.7457	Intermediate Similarity	NPD7298	Approved
0.7444	Intermediate Similarity	NPD8252	Approved
0.7444	Intermediate Similarity	NPD8099	Discontinued
0.7444	Intermediate Similarity	NPD8251	Approved
0.7438	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3687	Approved
0.7427	Intermediate Similarity	NPD3686	Approved
0.7421	Intermediate Similarity	NPD2974	Approved
0.7421	Intermediate Similarity	NPD2975	Approved
0.7421	Intermediate Similarity	NPD2973	Approved
0.7418	Intermediate Similarity	NPD6297	Approved
0.7368	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5177	Phase 3
0.7358	Intermediate Similarity	NPD3450	Approved
0.7358	Intermediate Similarity	NPD2494	Approved
0.7358	Intermediate Similarity	NPD2493	Approved
0.7358	Intermediate Similarity	NPD3452	Approved
0.7353	Intermediate Similarity	NPD4123	Phase 3
0.7351	Intermediate Similarity	NPD6851	Approved
0.7351	Intermediate Similarity	NPD6853	Approved
0.7349	Intermediate Similarity	NPD1375	Discontinued
0.7346	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1753	Discontinued
0.733	Intermediate Similarity	NPD6788	Approved
0.7318	Intermediate Similarity	NPD4166	Phase 2
0.7308	Intermediate Similarity	NPD5313	Approved
0.7308	Intermediate Similarity	NPD5312	Approved
0.7306	Intermediate Similarity	NPD4580	Approved
0.7301	Intermediate Similarity	NPD2238	Phase 2
0.7283	Intermediate Similarity	NPD4005	Discontinued
0.7262	Intermediate Similarity	NPD4162	Approved
0.7258	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD2488	Approved
0.7249	Intermediate Similarity	NPD2490	Approved
0.7245	Intermediate Similarity	NPD4582	Approved
0.7245	Intermediate Similarity	NPD4583	Approved
0.7212	Intermediate Similarity	NPD823	Approved
0.7212	Intermediate Similarity	NPD817	Approved
0.7204	Intermediate Similarity	NPD2971	Approved
0.7204	Intermediate Similarity	NPD2968	Approved
0.7194	Intermediate Similarity	NPD4002	Approved
0.7194	Intermediate Similarity	NPD4004	Approved
0.7191	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6997	Phase 2
0.7182	Intermediate Similarity	NPD6688	Approved
0.7182	Intermediate Similarity	NPD6687	Approved
0.7178	Intermediate Similarity	NPD5718	Phase 2
0.7176	Intermediate Similarity	NPD2677	Approved
0.7176	Intermediate Similarity	NPD3692	Discontinued
0.7169	Intermediate Similarity	NPD6895	Approved
0.7169	Intermediate Similarity	NPD6896	Approved
0.7168	Intermediate Similarity	NPD4727	Phase 1
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7827	Phase 1
0.7159	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3705	Approved
0.7151	Intermediate Similarity	NPD1424	Approved
0.7143	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7047	Phase 3
0.7143	Intermediate Similarity	NPD4678	Approved
0.7135	Intermediate Similarity	NPD7124	Phase 2
0.7126	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5677	Discontinued
0.711	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7526	Approved
0.711	Intermediate Similarity	NPD52	Approved
0.7108	Intermediate Similarity	NPD2492	Phase 1
0.7097	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3124	Discontinued
0.7086	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4103	Phase 2
0.707	Intermediate Similarity	NPD1357	Approved
0.7069	Intermediate Similarity	NPD5976	Discontinued
0.7069	Intermediate Similarity	NPD2122	Discontinued
0.7056	Intermediate Similarity	NPD3057	Approved
0.7055	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7007	Discovery
0.7039	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1132	Approved
0.703	Intermediate Similarity	NPD1136	Approved
0.703	Intermediate Similarity	NPD2674	Phase 3
0.703	Intermediate Similarity	NPD1130	Approved
0.7021	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6090	Discontinued
0.7	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4055	Discovery
0.6994	Remote Similarity	NPD2421	Approved
0.6994	Remote Similarity	NPD2420	Approved
0.6994	Remote Similarity	NPD1774	Approved
0.6989	Remote Similarity	NPD3885	Approved
0.6988	Remote Similarity	NPD3109	Approved
0.6988	Remote Similarity	NPD3110	Approved
0.6982	Remote Similarity	NPD2161	Phase 2
0.6978	Remote Similarity	NPD7802	Discontinued
0.697	Remote Similarity	NPD601	Approved
0.697	Remote Similarity	NPD598	Approved
0.697	Remote Similarity	NPD3533	Approved
0.697	Remote Similarity	NPD597	Approved
0.697	Remote Similarity	NPD2972	Approved
0.6966	Remote Similarity	NPD3383	Approved
0.6966	Remote Similarity	NPD3382	Approved
0.6966	Remote Similarity	NPD3384	Approved
0.6961	Remote Similarity	NPD5709	Phase 3
0.6957	Remote Similarity	NPD4659	Approved
0.695	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5676	Approved
0.6941	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3122	Phase 3
0.6936	Remote Similarity	NPD3845	Phase 1
0.6935	Remote Similarity	NPD42	Phase 2
0.6935	Remote Similarity	NPD6042	Phase 2
0.6927	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4666	Phase 3
0.6923	Remote Similarity	NPD2904	Discontinued
0.6915	Remote Similarity	NPD7039	Approved
0.6915	Remote Similarity	NPD7038	Approved
0.6911	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6072	Discontinued
0.6905	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7037	Approved
0.6894	Remote Similarity	NPD2232	Approved
0.6894	Remote Similarity	NPD2233	Approved
0.6894	Remote Similarity	NPD2230	Approved
0.6893	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5978	Approved
0.6889	Remote Similarity	NPD5977	Approved
0.6886	Remote Similarity	NPD3062	Approved
0.6886	Remote Similarity	NPD3059	Approved
0.6886	Remote Similarity	NPD3061	Approved
0.6884	Remote Similarity	NPD2491	Approved
0.6884	Remote Similarity	NPD3448	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