NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.13
Volume:	220.093
LogP:	0.616
LogD:	0.653
LogS:	-0.969
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	4.069
Fsp3:	0.75
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:	-4.571
MDCK Permeability:	1.886748032120522e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.64
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.681
Plasma Protein Binding (PPB):	53.76338577270508%
Volume Distribution (VD):	0.456
Pgp-substrate:	47.04817199707031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	7.067
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.706
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.804
Carcinogencity:	0.956
Eye Corrosion:	0.101
Eye Irritation:	0.166
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC40687

Natural Product ID:	NPC40687
*Common Name:**	Calamusin I
IUPAC Name:	(4aS,5S,8S)-5,8-dihydroxy-4a,8-dimethyl-4,5,6,7-tetrahydro-3H-naphthalen-2-one
Synonyms:	Calamusin I
Standard InCHIKey:	QKBMWRGCXJWSPL-SRVKXCTJSA-N
Standard InCHI:	InChI=1S/C12H18O3/c1-11-5-3-8(13)7-9(11)12(2,15)6-4-10(11)14/h7,10,14-15H,3-6H2,1-2H3/t10-,11-,12-/m0/s1
SMILES:	C[C@]12CCC(=O)C=C1[C@](C)(CC[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063125
PubChem CID:	60156151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25682	Acorus calamus	Species	Acoraceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[552030]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[552030]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[552030]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[552030]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[552030]

☑ 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 NPC40687 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	174
0.1-0.2	1230
0.2-0.3	4930
0.3-0.4	9965
0.4-0.5	14467
0.5-0.6	7233
0.6-0.7	3953
0.7-0.8	691
0.8-0.85	40
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC169941
0.9136	High Similarity	NPC251475
0.9059	High Similarity	NPC134321
0.8837	High Similarity	NPC128672
0.875	High Similarity	NPC196227
0.8721	High Similarity	NPC472973
0.8675	High Similarity	NPC64600
0.8642	High Similarity	NPC308038
0.8642	High Similarity	NPC281138
0.859	High Similarity	NPC247586
0.8588	High Similarity	NPC472974
0.8554	High Similarity	NPC93590
0.8539	High Similarity	NPC472976
0.8539	High Similarity	NPC472977
0.8523	High Similarity	NPC472978
0.8523	High Similarity	NPC116726
0.8452	Intermediate Similarity	NPC66764
0.8452	Intermediate Similarity	NPC105173
0.8452	Intermediate Similarity	NPC110150
0.8444	Intermediate Similarity	NPC316215
0.8444	Intermediate Similarity	NPC134067
0.8409	Intermediate Similarity	NPC230332
0.8387	Intermediate Similarity	NPC470184
0.8372	Intermediate Similarity	NPC472985
0.8372	Intermediate Similarity	NPC472986
0.8315	Intermediate Similarity	NPC472975
0.8313	Intermediate Similarity	NPC148685
0.8313	Intermediate Similarity	NPC104120
0.8313	Intermediate Similarity	NPC157895
0.8313	Intermediate Similarity	NPC172013
0.8295	Intermediate Similarity	NPC472983
0.8293	Intermediate Similarity	NPC62336
0.8272	Intermediate Similarity	NPC263582
0.8261	Intermediate Similarity	NPC254496
0.8242	Intermediate Similarity	NPC259286
0.8222	Intermediate Similarity	NPC69454
0.8171	Intermediate Similarity	NPC197659
0.8171	Intermediate Similarity	NPC149550
0.8171	Intermediate Similarity	NPC85105
0.8171	Intermediate Similarity	NPC257666
0.8171	Intermediate Similarity	NPC74995
0.8171	Intermediate Similarity	NPC266193
0.8161	Intermediate Similarity	NPC473226
0.8152	Intermediate Similarity	NPC249954
0.814	Intermediate Similarity	NPC476412
0.8125	Intermediate Similarity	NPC118911
0.8111	Intermediate Similarity	NPC475441
0.8111	Intermediate Similarity	NPC73457
0.8111	Intermediate Similarity	NPC63748
0.809	Intermediate Similarity	NPC473100
0.8072	Intermediate Similarity	NPC178852
0.8072	Intermediate Similarity	NPC475994
0.8068	Intermediate Similarity	NPC471792
0.8065	Intermediate Similarity	NPC285513
0.8049	Intermediate Similarity	NPC472305
0.8046	Intermediate Similarity	NPC476426
0.8025	Intermediate Similarity	NPC215050
0.8	Intermediate Similarity	NPC48010
0.8	Intermediate Similarity	NPC119229
0.8	Intermediate Similarity	NPC470298
0.8	Intermediate Similarity	NPC226068
0.8	Intermediate Similarity	NPC115862
0.8	Intermediate Similarity	NPC473099
0.8	Intermediate Similarity	NPC84790
0.7978	Intermediate Similarity	NPC471793
0.7978	Intermediate Similarity	NPC58271
0.7978	Intermediate Similarity	NPC328539
0.7978	Intermediate Similarity	NPC158778
0.7978	Intermediate Similarity	NPC471791
0.7976	Intermediate Similarity	NPC152061
0.7957	Intermediate Similarity	NPC471463
0.7955	Intermediate Similarity	NPC470955
0.7952	Intermediate Similarity	NPC34110
0.7952	Intermediate Similarity	NPC203403
0.7935	Intermediate Similarity	NPC103527
0.7931	Intermediate Similarity	NPC470812
0.7931	Intermediate Similarity	NPC251170
0.7917	Intermediate Similarity	NPC473424
0.7912	Intermediate Similarity	NPC475806
0.7912	Intermediate Similarity	NPC172101
0.7912	Intermediate Similarity	NPC99380
0.7895	Intermediate Similarity	NPC472644
0.7889	Intermediate Similarity	NPC86319
0.7889	Intermediate Similarity	NPC309603
0.7889	Intermediate Similarity	NPC473999
0.7889	Intermediate Similarity	NPC275740
0.7882	Intermediate Similarity	NPC471514
0.7882	Intermediate Similarity	NPC472301
0.7879	Intermediate Similarity	NPC217201
0.7875	Intermediate Similarity	NPC173321
0.7872	Intermediate Similarity	NPC161147
0.7865	Intermediate Similarity	NPC472324
0.7865	Intermediate Similarity	NPC298904
0.7857	Intermediate Similarity	NPC472645
0.7849	Intermediate Similarity	NPC473170
0.7849	Intermediate Similarity	NPC266899
0.7849	Intermediate Similarity	NPC476245
0.7849	Intermediate Similarity	NPC474602
0.7849	Intermediate Similarity	NPC272617
0.7849	Intermediate Similarity	NPC271195
0.7841	Intermediate Similarity	NPC470574
0.7841	Intermediate Similarity	NPC197823
0.7841	Intermediate Similarity	NPC36350
0.7841	Intermediate Similarity	NPC15807
0.7831	Intermediate Similarity	NPC1973
0.7831	Intermediate Similarity	NPC470525
0.7831	Intermediate Similarity	NPC151622
0.7831	Intermediate Similarity	NPC167873
0.7831	Intermediate Similarity	NPC7629
0.7826	Intermediate Similarity	NPC477435
0.7826	Intermediate Similarity	NPC472930
0.7826	Intermediate Similarity	NPC477436
0.7826	Intermediate Similarity	NPC109305
0.7812	Intermediate Similarity	NPC302537
0.7812	Intermediate Similarity	NPC472637
0.7812	Intermediate Similarity	NPC163372
0.7812	Intermediate Similarity	NPC81530
0.78	Intermediate Similarity	NPC20192
0.78	Intermediate Similarity	NPC11710
0.7791	Intermediate Similarity	NPC473420
0.7778	Intermediate Similarity	NPC471722
0.7778	Intermediate Similarity	NPC474925
0.7778	Intermediate Similarity	NPC220229
0.7778	Intermediate Similarity	NPC143767
0.7778	Intermediate Similarity	NPC131470
0.7778	Intermediate Similarity	NPC104560
0.7778	Intermediate Similarity	NPC475060
0.7766	Intermediate Similarity	NPC117133
0.7765	Intermediate Similarity	NPC19900
0.7753	Intermediate Similarity	NPC194417
0.7753	Intermediate Similarity	NPC179591
0.7753	Intermediate Similarity	NPC82979
0.7753	Intermediate Similarity	NPC198761
0.7742	Intermediate Similarity	NPC470958
0.7742	Intermediate Similarity	NPC299100
0.7742	Intermediate Similarity	NPC474690
0.7742	Intermediate Similarity	NPC470957
0.7742	Intermediate Similarity	NPC212812
0.7742	Intermediate Similarity	NPC8993
0.7732	Intermediate Similarity	NPC136289
0.7732	Intermediate Similarity	NPC477915
0.7732	Intermediate Similarity	NPC119601
0.7732	Intermediate Similarity	NPC308726
0.7727	Intermediate Similarity	NPC227132
0.7717	Intermediate Similarity	NPC473998
0.7717	Intermediate Similarity	NPC168027
0.7717	Intermediate Similarity	NPC185936
0.7717	Intermediate Similarity	NPC233116
0.7711	Intermediate Similarity	NPC114236
0.7708	Intermediate Similarity	NPC154072
0.7708	Intermediate Similarity	NPC198880
0.7708	Intermediate Similarity	NPC476274
0.7701	Intermediate Similarity	NPC48362
0.7701	Intermediate Similarity	NPC38796
0.7701	Intermediate Similarity	NPC158411
0.7701	Intermediate Similarity	NPC279186
0.7701	Intermediate Similarity	NPC92226
0.7701	Intermediate Similarity	NPC70479
0.77	Intermediate Similarity	NPC65941
0.7692	Intermediate Similarity	NPC118011
0.7692	Intermediate Similarity	NPC472971
0.7692	Intermediate Similarity	NPC36668
0.7692	Intermediate Similarity	NPC123912
0.7692	Intermediate Similarity	NPC119416
0.7692	Intermediate Similarity	NPC472688
0.7692	Intermediate Similarity	NPC472676
0.7692	Intermediate Similarity	NPC472970
0.7684	Intermediate Similarity	NPC170131
0.7684	Intermediate Similarity	NPC471916
0.7684	Intermediate Similarity	NPC474343
0.7684	Intermediate Similarity	NPC474785
0.7684	Intermediate Similarity	NPC18509
0.7684	Intermediate Similarity	NPC474938
0.7683	Intermediate Similarity	NPC29542
0.7683	Intermediate Similarity	NPC201562
0.7683	Intermediate Similarity	NPC323437
0.7683	Intermediate Similarity	NPC186042
0.7677	Intermediate Similarity	NPC323834
0.7677	Intermediate Similarity	NPC214264
0.7677	Intermediate Similarity	NPC48733
0.7677	Intermediate Similarity	NPC32006
0.7677	Intermediate Similarity	NPC49958
0.7677	Intermediate Similarity	NPC202167
0.7677	Intermediate Similarity	NPC302607
0.7677	Intermediate Similarity	NPC50692
0.7677	Intermediate Similarity	NPC85829
0.7677	Intermediate Similarity	NPC171137
0.7677	Intermediate Similarity	NPC152695
0.7677	Intermediate Similarity	NPC149047
0.7677	Intermediate Similarity	NPC319077
0.7677	Intermediate Similarity	NPC260268
0.7677	Intermediate Similarity	NPC97202
0.7677	Intermediate Similarity	NPC476027
0.7677	Intermediate Similarity	NPC150531
0.7677	Intermediate Similarity	NPC296945
0.7677	Intermediate Similarity	NPC85529
0.7674	Intermediate Similarity	NPC2482
0.7667	Intermediate Similarity	NPC220930
0.7667	Intermediate Similarity	NPC475740
0.7667	Intermediate Similarity	NPC272039

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 NPC40687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1716
0.2-0.3	3873
0.3-0.4	2307
0.4-0.5	689
0.5-0.6	235
0.6-0.7	150
0.7-0.8	13
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
0.7889	Intermediate Similarity	NPD5328	Approved
0.7753	Intermediate Similarity	NPD3618	Phase 1
0.7732	Intermediate Similarity	NPD5211	Phase 2
0.7717	Intermediate Similarity	NPD6079	Approved
0.7684	Intermediate Similarity	NPD4755	Approved
0.764	Intermediate Similarity	NPD1696	Phase 3
0.7634	Intermediate Similarity	NPD4202	Approved
0.7576	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD4696	Approved
0.7526	Intermediate Similarity	NPD5285	Approved
0.7526	Intermediate Similarity	NPD5286	Approved
0.7526	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.7449	Intermediate Similarity	NPD5223	Approved
0.7396	Intermediate Similarity	NPD5222	Approved
0.7396	Intermediate Similarity	NPD4697	Phase 3
0.7396	Intermediate Similarity	NPD5221	Approved
0.7396	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5226	Approved
0.7374	Intermediate Similarity	NPD5224	Approved
0.7374	Intermediate Similarity	NPD5225	Approved
0.7374	Intermediate Similarity	NPD4633	Approved
0.734	Intermediate Similarity	NPD7515	Phase 2
0.7333	Intermediate Similarity	NPD3666	Approved
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD4786	Approved
0.732	Intermediate Similarity	NPD5173	Approved
0.73	Intermediate Similarity	NPD5175	Approved
0.73	Intermediate Similarity	NPD5174	Approved
0.73	Intermediate Similarity	NPD4754	Approved
0.7174	Intermediate Similarity	NPD4519	Discontinued
0.7174	Intermediate Similarity	NPD5279	Phase 3
0.7174	Intermediate Similarity	NPD4623	Approved
0.716	Intermediate Similarity	NPD7331	Phase 2
0.7157	Intermediate Similarity	NPD6402	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD4767	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD4768	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7087	Intermediate Similarity	NPD5697	Approved
0.7079	Intermediate Similarity	NPD4695	Discontinued
0.7079	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7341	Phase 2
0.7019	Intermediate Similarity	NPD5128	Approved
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.7019	Intermediate Similarity	NPD4729	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7019	Intermediate Similarity	NPD4730	Approved
0.701	Intermediate Similarity	NPD7748	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7902	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6947	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD4223	Phase 3
0.6923	Remote Similarity	NPD4221	Approved
0.6915	Remote Similarity	NPD3573	Approved
0.6887	Remote Similarity	NPD5135	Approved
0.6887	Remote Similarity	NPD4634	Approved
0.6887	Remote Similarity	NPD5247	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6887	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5169	Approved
0.6887	Remote Similarity	NPD5249	Phase 3
0.6887	Remote Similarity	NPD5248	Approved
0.6887	Remote Similarity	NPD5250	Approved
0.6887	Remote Similarity	NPD5251	Approved
0.6882	Remote Similarity	NPD1694	Approved
0.6822	Remote Similarity	NPD5216	Approved
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD5217	Approved
0.6822	Remote Similarity	NPD5215	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6822	Remote Similarity	NPD5127	Approved
0.6774	Remote Similarity	NPD3668	Phase 3
0.6774	Remote Similarity	NPD4197	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6759	Remote Similarity	NPD6882	Approved
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.6733	Remote Similarity	NPD4225	Approved
0.6705	Remote Similarity	NPD8264	Approved
0.6702	Remote Similarity	NPD5329	Approved
0.6698	Remote Similarity	NPD5168	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD5167	Approved
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6411	Approved
0.6632	Remote Similarity	NPD4694	Approved
0.6632	Remote Similarity	NPD4693	Phase 3
0.6632	Remote Similarity	NPD4688	Approved
0.6632	Remote Similarity	NPD4689	Approved
0.6632	Remote Similarity	NPD5205	Approved
0.6632	Remote Similarity	NPD4138	Approved
0.6632	Remote Similarity	NPD4690	Approved
0.6632	Remote Similarity	NPD5280	Approved
0.6632	Remote Similarity	NPD5690	Phase 2
0.66	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD5210	Approved
0.6577	Remote Similarity	NPD6274	Approved
0.6569	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD7525	Registered
0.6518	Remote Similarity	NPD6317	Approved
0.6518	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6465	Remote Similarity	NPD5281	Approved
0.6465	Remote Similarity	NPD5284	Approved
0.6463	Remote Similarity	NPD368	Approved
0.646	Remote Similarity	NPD6313	Approved
0.646	Remote Similarity	NPD6335	Approved
0.646	Remote Similarity	NPD6314	Approved
0.6458	Remote Similarity	NPD7521	Approved
0.6458	Remote Similarity	NPD7334	Approved
0.6458	Remote Similarity	NPD6684	Approved
0.6458	Remote Similarity	NPD5330	Approved
0.6458	Remote Similarity	NPD7146	Approved
0.6458	Remote Similarity	NPD6409	Approved
0.6444	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6422	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD7101	Approved
0.6404	Remote Similarity	NPD7100	Approved
0.6392	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4096	Approved
0.6354	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6054	Approved
0.6348	Remote Similarity	NPD6319	Approved
0.6348	Remote Similarity	NPD6059	Approved
0.6333	Remote Similarity	NPD6942	Approved
0.6333	Remote Similarity	NPD7339	Approved
0.6333	Remote Similarity	NPD3703	Phase 2
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6903	Approved
0.6327	Remote Similarity	NPD4518	Approved
0.6316	Remote Similarity	NPD4788	Approved
0.6304	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6909	Approved
0.6293	Remote Similarity	NPD6908	Approved
0.6293	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6015	Approved
0.6293	Remote Similarity	NPD5983	Phase 2
0.6293	Remote Similarity	NPD6016	Approved
0.6283	Remote Similarity	NPD6868	Approved
0.6277	Remote Similarity	NPD4139	Approved
0.6277	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD5988	Approved
0.6238	Remote Similarity	NPD5133	Approved
0.6237	Remote Similarity	NPD4195	Approved
0.6226	Remote Similarity	NPD7632	Discontinued
0.6222	Remote Similarity	NPD6924	Approved
0.6222	Remote Similarity	NPD6926	Approved
0.62	Remote Similarity	NPD5785	Approved
0.619	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5363	Approved
0.6186	Remote Similarity	NPD7604	Phase 2
0.6176	Remote Similarity	NPD5282	Discontinued
0.617	Remote Similarity	NPD7509	Discontinued
0.617	Remote Similarity	NPD6930	Phase 2
0.617	Remote Similarity	NPD4748	Discontinued
0.617	Remote Similarity	NPD6931	Approved
0.6163	Remote Similarity	NPD3704	Approved
0.6162	Remote Similarity	NPD6672	Approved
0.6162	Remote Similarity	NPD5737	Approved
0.6161	Remote Similarity	NPD6053	Discontinued
0.6147	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6412	Phase 2
0.6136	Remote Similarity	NPD4137	Phase 3

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